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69866-21-3

69866-21-3

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  • Benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxamide,7-[[1,6-dihydro-4-hydroxy-5-methoxy-7-[[(7bR,8aS)-4,5,8,8a-tetrahydro-7-methyl-4-oxocyclopropa[c]pyrrolo[3,2-e]indol-2(1H)-yl]carbonyl]benzo[1,2-b:4,3-b'

    Cas No: 69866-21-3

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  • Benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxamide,7-[[1,6-dihydro-4-hydroxy-5-methoxy-7-[[(7bR,8aS)-4,5,8,8a-tetrahydro-7-methyl-4-oxocyclopropa[c]pyrrolo[3,2-e]indol-2(1H)-yl]carbonyl]benzo[1,2-b:4,3-b'

    Cas No: 69866-21-3

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  • Benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxamide,7-[[1,6-dihydro-4-hydroxy-5-methoxy-7-[[(7bR,8aS)-4,5,8,8a-tetrahydro-7-methyl-4-oxocyclopropa[c]pyrrolo[3,2-e]indol-2(1H)-yl]carbonyl]benzo[1,2-b:4,3-b'

    Cas No: 69866-21-3

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  • Benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxamide,7-[[1,6-dihydro-4-hydroxy-5-methoxy-7-[[(7bR,8aS)-4,5,8,8a-tetrahydro-7-methyl-4-oxocyclopropa[c]pyrrolo[3,2-e]indol-2(1H)-yl]carbonyl]benzo[1,2-b:4,3-b'

    Cas No: 69866-21-3

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  • Benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxamide,7-[[1,6-dihydro-4-hydroxy-5-methoxy-7-[[(7bR,8aS)-4,5,8,8a-tetrahydro-7-methyl-4-oxocyclopropa[c]pyrrolo[3,2-e]indol-2(1H)-yl]carbonyl]benzo[1,2-b:4,3-b'

    Cas No: 69866-21-3

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69866-21-3 Usage

Safety Profile

Deadly poison by intravenous andintraperitoneal routes. Mutation data reported. Whenheated to decomposition it emits toxic fumes of NOx.

Check Digit Verification of cas no

The CAS Registry Mumber 69866-21-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,9,8,6 and 6 respectively; the second part has 2 digits, 2 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 69866-21:
(7*6)+(6*9)+(5*8)+(4*6)+(3*6)+(2*2)+(1*1)=183
183 % 10 = 3
So 69866-21-3 is a valid CAS Registry Number.
InChI:InChI=1/C37H33N7O8/c1-14-12-39-27-22(45)10-23-37(24(14)27)11-15(37)13-44(23)35(49)21-9-18-16-4-6-42(28(16)30(46)32(51-2)25(18)41-21)34(48)20-8-19-17-5-7-43(36(38)50)29(17)31(47)33(52-3)26(19)40-20/h8-10,12,15,39-41,46-47H,4-7,11,13H2,1-3H3,(H2,38,50)

69866-21-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name Benzo[1,2-b_4,3-b']dipyrrole-3(2H)-carboxamide, 7-[[1,6-dihydro-4-hydroxy-5-methoxy-7-[(4,5,8,8a-tetrahydro-7-methyl-4-oxocyclopropa[c]pyrrolo[3,2-e]indol-2(1H)-yl)carbonyl]benzo[1,2-b_4,3-b']dipyrrol-3(2H)-yl]carbonyl]-1,6-dihydro-4-hydroxy-5-methoxy-

1.2 Other means of identification

Product number -
Other names (+)-(3bR,4aS)-CC-1065

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:69866-21-3 SDS

69866-21-3Synthetic route

C37H34ClN7O8
112764-71-3

C37H34ClN7O8

CC-1065
69866-21-3

CC-1065

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 4h; Ambient temperature;45%
With triethylamine In water; acetonitrile at 22℃; for 0.5h;43%
With triethylamine In water; acetonitrile at 23℃; for 0.5h; Yield given;
With triethylamine In water; acetonitrile for 1h; Ambient temperature; Yield given;
tert-butyl-(1S)-1-(chloromethyl)-5-hydroxy-8-methyl-1,6-dihydropyrrolo[3,2-e]indole-3(2H)-carboxylate
110314-51-7

tert-butyl-(1S)-1-(chloromethyl)-5-hydroxy-8-methyl-1,6-dihydropyrrolo[3,2-e]indole-3(2H)-carboxylate

CC-1065
69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 3M HCl / ethyl acetate / 1 h / Ambient temperature
2: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature
3: 45 percent / DBU / acetonitrile / 4 h / Ambient temperature
View Scheme
Multi-step reaction with 3 steps
1: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C
2: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
3: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme
Multi-step reaction with 3 steps
1: 3N HCl / ethyl acetate / 0.75 h / 23 °C
2: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C
3: Et3N / H2O; acetonitrile / 0.5 h / 23 °C
View Scheme
Multi-step reaction with 3 steps
1: hydrogen chloride gas / ethyl acetate / 0.67 h
2: 54 percent / EDC / N,N-dimethyl-acetamide / 2 h / Ambient temperature
3: triethylamine / acetonitrile; H2O / 1 h / Ambient temperature
View Scheme
(S)-1,6-dihydro-1-(hydroxymethyl)-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester
112836-67-6

(S)-1,6-dihydro-1-(hydroxymethyl)-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester

CC-1065
69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 82 percent / PPh3, CCl4 / CH2Cl2 / 7 h / Ambient temperature
2: 88 percent / 25percent HCO2NH4 / 10percentPd-C / tetrahydrofuran / 6 h / 0 °C
3: 3M HCl / ethyl acetate / 1 h / Ambient temperature
4: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature
5: 45 percent / DBU / acetonitrile / 4 h / Ambient temperature
View Scheme
Multi-step reaction with 5 steps
1: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C
2: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C
3: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C
4: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
5: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme
Multi-step reaction with 5 steps
1: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C
2: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C
3: 3N HCl / ethyl acetate / 0.75 h / 23 °C
4: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C
5: Et3N / H2O; acetonitrile / 0.5 h / 23 °C
View Scheme
Multi-step reaction with 6 steps
1: pyridine / 6 h / Ambient temperature
2: lithium chloride / dimethylformamide / 0.42 h / 80 °C
3: ammonium formate / 10percent Pd/C / tetrahydrofuran; methanol / 0.33 h / Ambient temperature
4: hydrogen chloride gas / ethyl acetate / 0.67 h
5: 54 percent / EDC / N,N-dimethyl-acetamide / 2 h / Ambient temperature
6: triethylamine / acetonitrile; H2O / 1 h / Ambient temperature
View Scheme
(S)-1-(chloromethyl)-1,6-dihydro-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester
110314-50-6

(S)-1-(chloromethyl)-1,6-dihydro-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester

CC-1065
69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 88 percent / 25percent HCO2NH4 / 10percentPd-C / tetrahydrofuran / 6 h / 0 °C
2: 3M HCl / ethyl acetate / 1 h / Ambient temperature
3: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature
4: 45 percent / DBU / acetonitrile / 4 h / Ambient temperature
View Scheme
Multi-step reaction with 4 steps
1: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C
2: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C
3: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
4: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme
Multi-step reaction with 4 steps
1: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C
2: 3N HCl / ethyl acetate / 0.75 h / 23 °C
3: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C
4: Et3N / H2O; acetonitrile / 0.5 h / 23 °C
View Scheme
Multi-step reaction with 4 steps
1: ammonium formate / 10percent Pd/C / tetrahydrofuran; methanol / 0.33 h / Ambient temperature
2: hydrogen chloride gas / ethyl acetate / 0.67 h
3: 54 percent / EDC / N,N-dimethyl-acetamide / 2 h / Ambient temperature
4: triethylamine / acetonitrile; H2O / 1 h / Ambient temperature
View Scheme
(S)-1-(chloromethyl)-1,6-dihydro-5-hydroxy-8-methylbenzo[1,2-b:4,3-b']dipyrrole hydrochloride
110314-54-0

(S)-1-(chloromethyl)-1,6-dihydro-5-hydroxy-8-methylbenzo[1,2-b:4,3-b']dipyrrole hydrochloride

CC-1065
69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature
2: 45 percent / DBU / acetonitrile / 4 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
2: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme
Multi-step reaction with 2 steps
1: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C
2: Et3N / H2O; acetonitrile / 0.5 h / 23 °C
View Scheme
Multi-step reaction with 2 steps
1: 54 percent / EDC / N,N-dimethyl-acetamide / 2 h / Ambient temperature
2: triethylamine / acetonitrile; H2O / 1 h / Ambient temperature
View Scheme
(3S)-3-acetoxymethyl-5-amino-6-benzyloxy-1-(t-butoxycarbonyl)-2,3-dihydroindole

(3S)-3-acetoxymethyl-5-amino-6-benzyloxy-1-(t-butoxycarbonyl)-2,3-dihydroindole

CC-1065
69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 96 percent / methanol / 0 deg C - r.t., overnight
2: 23 percent / Pd(OAc)2 / N,N-dimethyl-acetamide / 70 °C
3: 48 percent / Me2SBH3 / tetrahydrofuran / 19 h / Heating
4: 82 percent / PPh3, CCl4 / CH2Cl2 / 7 h / Ambient temperature
5: 88 percent / 25percent HCO2NH4 / 10percentPd-C / tetrahydrofuran / 6 h / 0 °C
6: 3M HCl / ethyl acetate / 1 h / Ambient temperature
7: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature
8: 45 percent / DBU / acetonitrile / 4 h / Ambient temperature
View Scheme
(S)-8-Acetoxymethyl-4-benzyloxy-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1,6-dicarboxylic acid 6-tert-butyl ester 1-methyl ester
176685-39-5

(S)-8-Acetoxymethyl-4-benzyloxy-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1,6-dicarboxylic acid 6-tert-butyl ester 1-methyl ester

CC-1065
69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 48 percent / Me2SBH3 / tetrahydrofuran / 19 h / Heating
2: 82 percent / PPh3, CCl4 / CH2Cl2 / 7 h / Ambient temperature
3: 88 percent / 25percent HCO2NH4 / 10percentPd-C / tetrahydrofuran / 6 h / 0 °C
4: 3M HCl / ethyl acetate / 1 h / Ambient temperature
5: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature
6: 45 percent / DBU / acetonitrile / 4 h / Ambient temperature
View Scheme
(S)-3-Acetoxymethyl-6-benzyloxy-5-((E)-2-methoxycarbonyl-vinylamino)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester
176685-38-4

(S)-3-Acetoxymethyl-6-benzyloxy-5-((E)-2-methoxycarbonyl-vinylamino)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester

CC-1065
69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 23 percent / Pd(OAc)2 / N,N-dimethyl-acetamide / 70 °C
2: 48 percent / Me2SBH3 / tetrahydrofuran / 19 h / Heating
3: 82 percent / PPh3, CCl4 / CH2Cl2 / 7 h / Ambient temperature
4: 88 percent / 25percent HCO2NH4 / 10percentPd-C / tetrahydrofuran / 6 h / 0 °C
5: 3M HCl / ethyl acetate / 1 h / Ambient temperature
6: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature
7: 45 percent / DBU / acetonitrile / 4 h / Ambient temperature
View Scheme
N-(2-hydroxy-4-nitrophenyl)benzamide
38880-89-6

N-(2-hydroxy-4-nitrophenyl)benzamide

CC-1065
69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 18 steps
1: 94 percent / K2CO3 / n-Bu4NI / acetone / 16 h / Heating
2: 90 percent / Na2S2O4 / tetrahydrofuran; H2O / 30 h / Heating
3: pyridine / tetrahydrofuran / 18 h / 22 °C
4: 84 percent / lead tetraacetate / benzene / 8 h / 22 °C
5: CH2Cl2 / 10 h / 23 °C
6: 10percent aq. hydrochloric acid / tetrahydrofuran / 20 h / 23 °C
7: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C
8: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h
9: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating
10: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min
11: 83 percent / acetyl chloride / methanol / 2 h / 50 °C
12: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C
13: tetrahydrofuran / 20 h / 23 °C
14: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C
15: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C
16: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C
17: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
18: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme
N-[4-[(Z)-Benzenesulfonylimino]-2-benzyloxy-cyclohexa-2,5-dien-(Z)-ylidene]-benzamide
112764-62-2

N-[4-[(Z)-Benzenesulfonylimino]-2-benzyloxy-cyclohexa-2,5-dien-(Z)-ylidene]-benzamide

CC-1065
69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1: 2.) 10percent aq. HCl / 1.) CH2Cl2, 0 - 23 deg C, 12 h 2.) THF, 23 deg C, 12 h
2: 97 percent / N-bromosuccinimide / H2SO4 / tetrahydrofuran / 1 h / -23 °C
3: 1.) NaH / 1.) DMF, 23 deg C, 15 min 2.) DMF, 23 deg C, 3 h
4: n-Bu3SnH / AIBN / benzene / 5 h / 80 °C
5: 1.) BH3*SMe2 2.) 2N aq. NaOH, 30percent H2O2 / 1.) THF, 0 - 23 deg C, 1 - 3 h 2.) 45 deg C, 30 min
6: 83 percent / 5percent HCl / methanol / 2 h / 50 °C
7: sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 3 h / 100 °C
8: tetrahydrofuran / 3 h / 23 °C
9: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C
10: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C
11: 3N HCl / ethyl acetate / 0.75 h / 23 °C
12: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C
13: Et3N / H2O; acetonitrile / 0.5 h / 23 °C
View Scheme
5-amino-1-benzoyl-7-(benzyloxy)-3-methyl-N5-(phenylsulfonyl)indole
112764-63-3

5-amino-1-benzoyl-7-(benzyloxy)-3-methyl-N5-(phenylsulfonyl)indole

CC-1065
69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C
2: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h
3: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating
4: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min
5: 83 percent / acetyl chloride / methanol / 2 h / 50 °C
6: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C
7: tetrahydrofuran / 20 h / 23 °C
8: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C
9: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C
10: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C
11: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
12: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme
Multi-step reaction with 12 steps
1: 97 percent / N-bromosuccinimide / H2SO4 / tetrahydrofuran / 1 h / -23 °C
2: 1.) NaH / 1.) DMF, 23 deg C, 15 min 2.) DMF, 23 deg C, 3 h
3: n-Bu3SnH / AIBN / benzene / 5 h / 80 °C
4: 1.) BH3*SMe2 2.) 2N aq. NaOH, 30percent H2O2 / 1.) THF, 0 - 23 deg C, 1 - 3 h 2.) 45 deg C, 30 min
5: 83 percent / 5percent HCl / methanol / 2 h / 50 °C
6: sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 3 h / 100 °C
7: tetrahydrofuran / 3 h / 23 °C
8: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C
9: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C
10: 3N HCl / ethyl acetate / 0.75 h / 23 °C
11: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C
12: Et3N / H2O; acetonitrile / 0.5 h / 23 °C
View Scheme
6-(6-Carbamoyl-5-hydroxy-4-methoxy-3,6,7,8-tetrahydro-pyrrolo[3,2-e]indole-2-carbonyl)-5-hydroxy-4-methoxy-3,6,7,8-tetrahydro-pyrrolo[3,2-e]indole-2-carboxylic acid
98296-23-2

6-(6-Carbamoyl-5-hydroxy-4-methoxy-3,6,7,8-tetrahydro-pyrrolo[3,2-e]indole-2-carbonyl)-5-hydroxy-4-methoxy-3,6,7,8-tetrahydro-pyrrolo[3,2-e]indole-2-carboxylic acid

CC-1065
69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
2: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme
Multi-step reaction with 2 steps
1: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C
2: Et3N / H2O; acetonitrile / 0.5 h / 23 °C
View Scheme
N-(4-Amino-2-benzyloxy-phenyl)-benzamide
112764-73-5

N-(4-Amino-2-benzyloxy-phenyl)-benzamide

CC-1065
69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 16 steps
1: pyridine / tetrahydrofuran / 18 h / 22 °C
2: 84 percent / lead tetraacetate / benzene / 8 h / 22 °C
3: CH2Cl2 / 10 h / 23 °C
4: 10percent aq. hydrochloric acid / tetrahydrofuran / 20 h / 23 °C
5: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C
6: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h
7: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating
8: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min
9: 83 percent / acetyl chloride / methanol / 2 h / 50 °C
10: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C
11: tetrahydrofuran / 20 h / 23 °C
12: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C
13: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C
14: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C
15: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
16: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme
N-(2-Benzyloxy-4-nitro-phenyl)-benzamide
112764-72-4

N-(2-Benzyloxy-4-nitro-phenyl)-benzamide

CC-1065
69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 17 steps
1: 90 percent / Na2S2O4 / tetrahydrofuran; H2O / 30 h / Heating
2: pyridine / tetrahydrofuran / 18 h / 22 °C
3: 84 percent / lead tetraacetate / benzene / 8 h / 22 °C
4: CH2Cl2 / 10 h / 23 °C
5: 10percent aq. hydrochloric acid / tetrahydrofuran / 20 h / 23 °C
6: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C
7: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h
8: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating
9: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min
10: 83 percent / acetyl chloride / methanol / 2 h / 50 °C
11: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C
12: tetrahydrofuran / 20 h / 23 °C
13: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C
14: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C
15: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C
16: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
17: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme
N-<4-(benzoylimino)-3-(benzyloxy)-2,5-cyclohexadien-1-ylidene>benzenesulfonamide

N-<4-(benzoylimino)-3-(benzyloxy)-2,5-cyclohexadien-1-ylidene>benzenesulfonamide

CC-1065
69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1: CH2Cl2 / 10 h / 23 °C
2: 10percent aq. hydrochloric acid / tetrahydrofuran / 20 h / 23 °C
3: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C
4: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h
5: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating
6: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min
7: 83 percent / acetyl chloride / methanol / 2 h / 50 °C
8: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C
9: tetrahydrofuran / 20 h / 23 °C
10: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C
11: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C
12: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C
13: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
14: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme
N-(4-Benzenesulfonylamino-2-benzyloxy-phenyl)-benzamide
112764-74-6

N-(4-Benzenesulfonylamino-2-benzyloxy-phenyl)-benzamide

CC-1065
69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 15 steps
1: 84 percent / lead tetraacetate / benzene / 8 h / 22 °C
2: CH2Cl2 / 10 h / 23 °C
3: 10percent aq. hydrochloric acid / tetrahydrofuran / 20 h / 23 °C
4: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C
5: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h
6: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating
7: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min
8: 83 percent / acetyl chloride / methanol / 2 h / 50 °C
9: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C
10: tetrahydrofuran / 20 h / 23 °C
11: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C
12: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C
13: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C
14: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
15: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme
N-(1-Benzoyl-7-benzyloxy-3-methyl-2-piperidin-1-yl-2,3-dihydro-1H-indol-5-yl)-benzenesulfonamide

N-(1-Benzoyl-7-benzyloxy-3-methyl-2-piperidin-1-yl-2,3-dihydro-1H-indol-5-yl)-benzenesulfonamide

CC-1065
69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1: 10percent aq. hydrochloric acid / tetrahydrofuran / 20 h / 23 °C
2: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C
3: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h
4: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating
5: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min
6: 83 percent / acetyl chloride / methanol / 2 h / 50 °C
7: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C
8: tetrahydrofuran / 20 h / 23 °C
9: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C
10: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C
11: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C
12: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
13: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme
PDE I dimer methyl ester
107890-45-9

PDE I dimer methyl ester

CC-1065
69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 84 percent / sodium dithionite, lithium hydroxide / tetrahydrofuran; methanol; H2O / 10 h / 45 °C
2: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
3: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme
Multi-step reaction with 3 steps
1: 84 percent / LiOH, Na2S2O4, water / tetrahydrofuran; methanol / 10 h / 45 °C
2: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C
3: Et3N / H2O; acetonitrile / 0.5 h / 23 °C
View Scheme
5-(benzyloxy)-1,2,3,6-tetrahydro-8-methylbenzo<1,2-b:4,3-b'>dipyrrole-1-methanol
112243-83-1

5-(benzyloxy)-1,2,3,6-tetrahydro-8-methylbenzo<1,2-b:4,3-b'>dipyrrole-1-methanol

CC-1065
69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: tetrahydrofuran / 20 h / 23 °C
2: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C
3: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C
4: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C
5: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
6: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme
Multi-step reaction with 6 steps
1: tetrahydrofuran / 3 h / 23 °C
2: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C
3: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C
4: 3N HCl / ethyl acetate / 0.75 h / 23 °C
5: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C
6: Et3N / H2O; acetonitrile / 0.5 h / 23 °C
View Scheme
(1RS)-3-(Benzenesulfonyl)-5-(benzyloxy)-1-(hydroxymethyl)-8-methyl-1,2-dihydro-3H-pyrrolo<3,2-e>indole
112764-67-7

(1RS)-3-(Benzenesulfonyl)-5-(benzyloxy)-1-(hydroxymethyl)-8-methyl-1,2-dihydro-3H-pyrrolo<3,2-e>indole

CC-1065
69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C
2: tetrahydrofuran / 20 h / 23 °C
3: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C
4: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C
5: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C
6: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
7: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme
Multi-step reaction with 7 steps
1: sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 3 h / 100 °C
2: tetrahydrofuran / 3 h / 23 °C
3: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C
4: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C
5: 3N HCl / ethyl acetate / 0.75 h / 23 °C
6: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C
7: Et3N / H2O; acetonitrile / 0.5 h / 23 °C
View Scheme
5-amino-1-benzoyl-7-(benzyloxy)-4-bromo-3-methyl-N5-(phenylsulfonyl)indole
112764-64-4

5-amino-1-benzoyl-7-(benzyloxy)-4-bromo-3-methyl-N5-(phenylsulfonyl)indole

CC-1065
69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h
2: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating
3: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min
4: 83 percent / acetyl chloride / methanol / 2 h / 50 °C
5: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C
6: tetrahydrofuran / 20 h / 23 °C
7: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C
8: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C
9: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C
10: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
11: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme
Multi-step reaction with 11 steps
1: 1.) NaH / 1.) DMF, 23 deg C, 15 min 2.) DMF, 23 deg C, 3 h
2: n-Bu3SnH / AIBN / benzene / 5 h / 80 °C
3: 1.) BH3*SMe2 2.) 2N aq. NaOH, 30percent H2O2 / 1.) THF, 0 - 23 deg C, 1 - 3 h 2.) 45 deg C, 30 min
4: 83 percent / 5percent HCl / methanol / 2 h / 50 °C
5: sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 3 h / 100 °C
6: tetrahydrofuran / 3 h / 23 °C
7: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C
8: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C
9: 3N HCl / ethyl acetate / 0.75 h / 23 °C
10: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C
11: Et3N / H2O; acetonitrile / 0.5 h / 23 °C
View Scheme
6-benzoyl-5-(benzyloxy)-1,2-dihydro-8-methyl-1-methylidene-3-(phenylsulfonyl)-3H-pyrrolo<3,2-e>indole
112793-55-2

6-benzoyl-5-(benzyloxy)-1,2-dihydro-8-methyl-1-methylidene-3-(phenylsulfonyl)-3H-pyrrolo<3,2-e>indole

CC-1065
69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min
2: 83 percent / acetyl chloride / methanol / 2 h / 50 °C
3: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C
4: tetrahydrofuran / 20 h / 23 °C
5: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C
6: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C
7: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C
8: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
9: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme
Multi-step reaction with 9 steps
1: 1.) BH3*SMe2 2.) 2N aq. NaOH, 30percent H2O2 / 1.) THF, 0 - 23 deg C, 1 - 3 h 2.) 45 deg C, 30 min
2: 83 percent / 5percent HCl / methanol / 2 h / 50 °C
3: sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 3 h / 100 °C
4: tetrahydrofuran / 3 h / 23 °C
5: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C
6: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C
7: 3N HCl / ethyl acetate / 0.75 h / 23 °C
8: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C
9: Et3N / H2O; acetonitrile / 0.5 h / 23 °C
View Scheme
6-benzoyl-5-(benzyloxy)-1,2-dihydro-1-(hydroxymethyl)-8-methyl-3-(phenylsulfonyl)-3H-pyrrolo<3,2-e>indole
112764-66-6

6-benzoyl-5-(benzyloxy)-1,2-dihydro-1-(hydroxymethyl)-8-methyl-3-(phenylsulfonyl)-3H-pyrrolo<3,2-e>indole

CC-1065
69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 83 percent / acetyl chloride / methanol / 2 h / 50 °C
2: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C
3: tetrahydrofuran / 20 h / 23 °C
4: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C
5: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C
6: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C
7: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
8: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme
Multi-step reaction with 8 steps
1: 83 percent / 5percent HCl / methanol / 2 h / 50 °C
2: sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 3 h / 100 °C
3: tetrahydrofuran / 3 h / 23 °C
4: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C
5: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C
6: 3N HCl / ethyl acetate / 0.75 h / 23 °C
7: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C
8: Et3N / H2O; acetonitrile / 0.5 h / 23 °C
View Scheme
1-benzoyl-7-(benzyloxy)-4-bromo-3-methyl-N5-(phenylsulfonyl)-5-(2-propyn-1-ylamino)indole
112764-65-5

1-benzoyl-7-(benzyloxy)-4-bromo-3-methyl-N5-(phenylsulfonyl)-5-(2-propyn-1-ylamino)indole

CC-1065
69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating
2: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min
3: 83 percent / acetyl chloride / methanol / 2 h / 50 °C
4: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C
5: tetrahydrofuran / 20 h / 23 °C
6: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C
7: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C
8: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C
9: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
10: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme
Multi-step reaction with 10 steps
1: n-Bu3SnH / AIBN / benzene / 5 h / 80 °C
2: 1.) BH3*SMe2 2.) 2N aq. NaOH, 30percent H2O2 / 1.) THF, 0 - 23 deg C, 1 - 3 h 2.) 45 deg C, 30 min
3: 83 percent / 5percent HCl / methanol / 2 h / 50 °C
4: sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 3 h / 100 °C
5: tetrahydrofuran / 3 h / 23 °C
6: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C
7: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C
8: 3N HCl / ethyl acetate / 0.75 h / 23 °C
9: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C
10: Et3N / H2O; acetonitrile / 0.5 h / 23 °C
View Scheme
2-Amino-5-nitrophenol
121-88-0

2-Amino-5-nitrophenol

CC-1065
69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 19 steps
1: 92 percent / K2CO3 / 4-(dimethylamino)pyridine / tetrahydrofuran / 4 h / 23 °C
2: 94 percent / K2CO3 / n-Bu4NI / acetone / 16 h / Heating
3: 90 percent / Na2S2O4 / tetrahydrofuran; H2O / 30 h / Heating
4: pyridine / tetrahydrofuran / 18 h / 22 °C
5: 84 percent / lead tetraacetate / benzene / 8 h / 22 °C
6: CH2Cl2 / 10 h / 23 °C
7: 10percent aq. hydrochloric acid / tetrahydrofuran / 20 h / 23 °C
8: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C
9: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h
10: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating
11: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min
12: 83 percent / acetyl chloride / methanol / 2 h / 50 °C
13: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C
14: tetrahydrofuran / 20 h / 23 °C
15: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C
16: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C
17: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C
18: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
19: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme
((S)-5-Benzyloxy-8-methyl-1,2,3,6-tetrahydro-pyrrolo[3,2-e]indol-1-yl)-methanol
108833-14-3

((S)-5-Benzyloxy-8-methyl-1,2,3,6-tetrahydro-pyrrolo[3,2-e]indol-1-yl)-methanol

CC-1065
69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: triethylamine / tetrahydrofuran / 90 h
2: pyridine / 6 h / Ambient temperature
3: lithium chloride / dimethylformamide / 0.42 h / 80 °C
4: ammonium formate / 10percent Pd/C / tetrahydrofuran; methanol / 0.33 h / Ambient temperature
5: hydrogen chloride gas / ethyl acetate / 0.67 h
6: 54 percent / EDC / N,N-dimethyl-acetamide / 2 h / Ambient temperature
7: triethylamine / acetonitrile; H2O / 1 h / Ambient temperature
View Scheme
((S)-5-Benzyloxy-3-methanesulfonyl-8-methyl-1,2,3,6-tetrahydro-pyrrolo[3,2-e]indol-1-yl)-methanol
101222-79-1

((S)-5-Benzyloxy-3-methanesulfonyl-8-methyl-1,2,3,6-tetrahydro-pyrrolo[3,2-e]indol-1-yl)-methanol

CC-1065
69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 3.4 M REDAL / tetrahydrofuran; toluene / 0.5 h / 85 °C
2: triethylamine / tetrahydrofuran / 90 h
3: pyridine / 6 h / Ambient temperature
4: lithium chloride / dimethylformamide / 0.42 h / 80 °C
5: ammonium formate / 10percent Pd/C / tetrahydrofuran; methanol / 0.33 h / Ambient temperature
6: hydrogen chloride gas / ethyl acetate / 0.67 h
7: 54 percent / EDC / N,N-dimethyl-acetamide / 2 h / Ambient temperature
8: triethylamine / acetonitrile; H2O / 1 h / Ambient temperature
View Scheme
(S)-5-Benzyloxy-1-methanesulfonyloxymethyl-8-methyl-1,6-dihydro-2H-pyrrolo[3,2-e]indole-3-carboxylic acid tert-butyl ester
110314-49-3

(S)-5-Benzyloxy-1-methanesulfonyloxymethyl-8-methyl-1,6-dihydro-2H-pyrrolo[3,2-e]indole-3-carboxylic acid tert-butyl ester

CC-1065
69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: lithium chloride / dimethylformamide / 0.42 h / 80 °C
2: ammonium formate / 10percent Pd/C / tetrahydrofuran; methanol / 0.33 h / Ambient temperature
3: hydrogen chloride gas / ethyl acetate / 0.67 h
4: 54 percent / EDC / N,N-dimethyl-acetamide / 2 h / Ambient temperature
5: triethylamine / acetonitrile; H2O / 1 h / Ambient temperature
View Scheme
C18H15ClN2O5S

C18H15ClN2O5S

CC-1065
69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 15 steps
1.1: dichloromethane; dimethyl sulfoxide / 29 h / 0 °C
2.1: diisobutylaluminium hydride / toluene / 2.5 h / -78 °C
2.2: 2.5 h / -78 °C
3.1: dmap / acetonitrile / 1 h / 20 °C
4.1: sodium chlorite; 2-methyl-but-2-ene; sodium dihydrogenphosphate / tetrahydrofuran; water; tert-butyl alcohol / 12 h / 20 °C
5.1: dmap; dicyclohexyl-carbodiimide / N,N-dimethyl-formamide / 8 h / 20 °C
6.1: sodium cyanoborohydride; acetic acid / 1,2-dichloro-benzene / 8.5 h / 185 °C
7.1: sodium hydrogencarbonate / tetrahydrofuran / 0.33 h / 20 °C
8.1: boron trichloride / dichloromethane / 0.67 h / 0 °C
9.1: palladium 10% on activated carbon; hydrogen / ethanol / 17 h / 20 °C / 760.05 Torr
10.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 10 h / 20 °C
11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C
12.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; tetrahydrofuran / 4 h / 20 °C
12.2: 1 h / 20 °C
13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3.25 h / 20 °C
13.2: 4.17 h / 0 - 20 °C
14.1: hydrogen; 10 wt% Pd(OH)2 on carbon / tetrahydrofuran / 0.33 h / 20 °C
15.1: triethylamine / tetrahydrofuran / 1 h / 20 °C
View Scheme
C13H11N3O2

C13H11N3O2

CC-1065
69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1.1: diisobutylaluminium hydride / toluene / 2.5 h / -78 °C
1.2: 2.5 h / -78 °C
2.1: dmap / acetonitrile / 1 h / 20 °C
3.1: sodium chlorite; 2-methyl-but-2-ene; sodium dihydrogenphosphate / tetrahydrofuran; water; tert-butyl alcohol / 12 h / 20 °C
4.1: dmap; dicyclohexyl-carbodiimide / N,N-dimethyl-formamide / 8 h / 20 °C
5.1: sodium cyanoborohydride; acetic acid / 1,2-dichloro-benzene / 8.5 h / 185 °C
6.1: sodium hydrogencarbonate / tetrahydrofuran / 0.33 h / 20 °C
7.1: boron trichloride / dichloromethane / 0.67 h / 0 °C
8.1: palladium 10% on activated carbon; hydrogen / ethanol / 17 h / 20 °C / 760.05 Torr
9.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 10 h / 20 °C
10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C
11.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; tetrahydrofuran / 4 h / 20 °C
11.2: 1 h / 20 °C
12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3.25 h / 20 °C
12.2: 4.17 h / 0 - 20 °C
13.1: hydrogen; 10 wt% Pd(OH)2 on carbon / tetrahydrofuran / 0.33 h / 20 °C
14.1: triethylamine / tetrahydrofuran / 1 h / 20 °C
View Scheme
CC-1065
69866-21-3

CC-1065

C37H35N7O9

C37H35N7O9

Conditions
ConditionsYield
With water In aq. phosphate buffer; dimethyl sulfoxide at 25℃; pH=7.0; Reagent/catalyst; Enzymatic reaction;

69866-21-3Downstream Products

69866-21-3Relevant articles and documents

Total Synthesis of (+)-CC-1065 Utilizing Ring Expansion Reaction of Benzocyclobutenone Oxime Sulfonate

Imaizumi, Taku,Yamashita, Yumi,Nakazawa, Yuki,Okano, Kentaro,Sakata, Juri,Tokuyama, Hidetoshi

supporting information, p. 6185 - 6189 (2019/07/03)

An indole synthesis via ring expansion of benzocyclobutenone oxime sulfonate was developed. Utility of the indole synthesis was demonstrated by the total synthesis of (+)-CC-1065. The middle and right segments were constructed by a sequential ring expansion of the symmetrical benzo-bis-cyclobutenone. The left segment was also constructed via ring expansion of the methyl-substituted benzocyclobutenone oxime sulfonates. After condensation of these three segments, the dienone cyclopropane structure was formed to complete the total synthesis.

Sequence specificity of DNA alkylation by the unnatural enantiomer of CC-1065 and its synthetic analogues

Hurley,Warpehoski,Lee,McGovren,Scahill,Kelly,Mitchell,Wicnienski,Gebhard,Johnson,Bradford

, p. 4633 - 4649 (2007/10/02)

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