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247570-24-7

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247570-24-7 Usage

Uses

cis-4-(Boc-amino)cyclohexylamine can be used in agrochemical, pharmaceutical and dyestuff field.

Check Digit Verification of cas no

The CAS Registry Mumber 247570-24-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,4,7,5,7 and 0 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 247570-24:
(8*2)+(7*4)+(6*7)+(5*5)+(4*7)+(3*0)+(2*2)+(1*4)=147
147 % 10 = 7
So 247570-24-7 is a valid CAS Registry Number.

247570-24-7 Well-known Company Product Price

  • Brand
  • (Code)Product description
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  • Detail
  • Alfa Aesar

  • (H62925)  cis-4-(Boc-amino)cyclohexylamine, 97%   

  • 247570-24-7

  • 1g

  • 437.0CNY

  • Detail
  • Alfa Aesar

  • (H62925)  cis-4-(Boc-amino)cyclohexylamine, 97%   

  • 247570-24-7

  • 5g

  • 1638.0CNY

  • Detail
  • Alfa Aesar

  • (H62925)  cis-4-(Boc-amino)cyclohexylamine, 97%   

  • 247570-24-7

  • 25g

  • 6552.0CNY

  • Detail

247570-24-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name cis tert-Butyl 4-aminocyclohexylcarbamate

1.2 Other means of identification

Product number -
Other names (4-{[(tert-butoxy)carbonyl]aMino}cyclohexyl)azanylidene

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:247570-24-7 SDS

247570-24-7Synthetic route

tert-butyl ((1S,4S)-4-(1,3-dioxoisoindolin-2-yl)cyclohexyl)carbamate
798551-43-6

tert-butyl ((1S,4S)-4-(1,3-dioxoisoindolin-2-yl)cyclohexyl)carbamate

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

Conditions
ConditionsYield
With hydrazine hydrate In ethanol at 80℃; for 2h;96%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

cis-1,4-cyclohexanediamine
15827-56-2

cis-1,4-cyclohexanediamine

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

Conditions
ConditionsYield
Stage #1: cis-1,4-cyclohexanediamine With hydrogenchloride In methanol at 20℃; for 1h;
Stage #2: di-tert-butyl dicarbonate In methanol at 20℃; for 1.16667h;
66.78%
(cis-4-azido-cyclohexyl)-carbamic acid tert-butyl ester
247568-84-9

(cis-4-azido-cyclohexyl)-carbamic acid tert-butyl ester

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

Conditions
ConditionsYield
With hydrogen; 5% palladium-on-charcoal In methanol under 760.051 Torr; for 2h;64%
With hydrogen; 5%-palladium/activated carbon In methanol; toluene at 20℃; under 60804.1 Torr; for 18h;
With hydrogen; 5%-palladium/activated carbon In methanol; toluene at 20℃; under 60804.1 Torr; for 18h;
cis-(4-tert-butoxycarbonylamino-cyclohexyl)-carbamic acid benzyl ester
509143-03-7

cis-(4-tert-butoxycarbonylamino-cyclohexyl)-carbamic acid benzyl ester

benzyl alcohol
100-51-6

benzyl alcohol

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

Conditions
ConditionsYield
With hydrogen; palladium 10% on activated carbon In ethanol58%
BOC-aminoether

BOC-aminoether

trans-1,4-diaminocyclohexane
3114-70-3

trans-1,4-diaminocyclohexane

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

Conditions
ConditionsYield
In methanol at 20℃; for 159.84h;
(±)-cis-N1-benzyloxycarbonyl-1,4-cyclohexanediamine
149423-70-1

(±)-cis-N1-benzyloxycarbonyl-1,4-cyclohexanediamine

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dichloromethane / 1 h
2: palladium 10% on activated carbon; hydrogen / methanol
View Scheme
cis-(4-tert-butoxycarbonylamino-cyclohexyl)-carbamic acid benzyl ester
509143-03-7

cis-(4-tert-butoxycarbonylamino-cyclohexyl)-carbamic acid benzyl ester

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dichloromethane / 1 h
2: palladium 10% on activated carbon; hydrogen / methanol
View Scheme
Multi-step reaction with 3 steps
1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
3: hydrazine hydrate / ethanol / 2 h / 80 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium hydroxide / tetrahydrofuran; water / 0 - 20 °C
2: diphenyl phosphoryl azide; triethylamine / toluene / 4 h / 45 - 55 °C
3: hydrogen / palladium 10% on activated carbon / ethanol
View Scheme
trans-tert-butyl 4-hydroxycyclohexylcarbamate
111300-06-2

trans-tert-butyl 4-hydroxycyclohexylcarbamate

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
2: hydrazine hydrate / ethanol / 2 h / 80 °C
View Scheme
trans-4-hydroxycyclohexylamine
27489-62-9

trans-4-hydroxycyclohexylamine

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
3: hydrazine hydrate / ethanol / 2 h / 80 °C
View Scheme
cis-4-tert-butoxycarbonylaminocyclohexane-1-ylcarboxylic acid
53292-90-3

cis-4-tert-butoxycarbonylaminocyclohexane-1-ylcarboxylic acid

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: diphenyl phosphoryl azide; triethylamine / toluene / 4 h / 45 - 55 °C
2: hydrogen / palladium 10% on activated carbon / ethanol
View Scheme
cis-4-aminocyclohexane-1-carboxylic acid
3685-23-2

cis-4-aminocyclohexane-1-carboxylic acid

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide / tetrahydrofuran; water / 0 - 20 °C
2: diphenyl phosphoryl azide; triethylamine / toluene / 4 h / 45 - 55 °C
3: hydrogen / palladium 10% on activated carbon / ethanol
View Scheme
tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

6-bromo-2,4-dichloropyrido[2,3-d]pyrimidine
1234616-70-6

6-bromo-2,4-dichloropyrido[2,3-d]pyrimidine

tert-butyl ((1s,4s)-4-((6-bromo-2-chloropyrido[2,3-d]pyrimidin-4-yl)amino)cyclohexyl)carbamate

tert-butyl ((1s,4s)-4-((6-bromo-2-chloropyrido[2,3-d]pyrimidin-4-yl)amino)cyclohexyl)carbamate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 3h;100%
tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

5-(2-methyl-4-phenoxyphenyl)-4-oxo-4,5-dihydro-3H-1-thia-3,5,8-triazaacenaphthylene-2-carboxylic acid

5-(2-methyl-4-phenoxyphenyl)-4-oxo-4,5-dihydro-3H-1-thia-3,5,8-triazaacenaphthylene-2-carboxylic acid

N-((1S,4S)-4-aminocyclohexyl)-5-(2-methyl-4-phenoxyphenyl)-4-oxo-4,5-dihydro-3H-1-thia-3,5,8-triazaacenaphthylene-2-carboxamide

N-((1S,4S)-4-aminocyclohexyl)-5-(2-methyl-4-phenoxyphenyl)-4-oxo-4,5-dihydro-3H-1-thia-3,5,8-triazaacenaphthylene-2-carboxamide

Conditions
ConditionsYield
Stage #1: tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate; 5-(2-methyl-4-phenoxyphenyl)-4-oxo-4,5-dihydro-3H-1-thia-3,5,8-triazaacenaphthylene-2-carboxylic acid With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;
Stage #2: With hydrogenchloride In methanol; water
100%
tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

3,5-bis(trifluoromethyl)phenyl carboxylic acid chloride
785-56-8

3,5-bis(trifluoromethyl)phenyl carboxylic acid chloride

[cis-4-(3,5-bistrifluoromethyl-benzoylamino)-cyclohexyl]-carbamic acid tert-butyl ester

[cis-4-(3,5-bistrifluoromethyl-benzoylamino)-cyclohexyl]-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With triethylamine In benzene at 20℃; for 2h;99%
tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

2-chloro-5-fluoronicotinic acid
38186-88-8

2-chloro-5-fluoronicotinic acid

tert-butyl N-[(1s,4s)-4-(2-chloro-5-fluoronicotinamido)cyclohexyl]carbamate
582333-07-1

tert-butyl N-[(1s,4s)-4-(2-chloro-5-fluoronicotinamido)cyclohexyl]carbamate

Conditions
ConditionsYield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In tetrahydrofuran; acetonitrile at 0 - 25℃; Inert atmosphere;98%
Stage #1: 2-chloro-5-fluoronicotinic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 18.15h;
Stage #2: tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;
tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

2,4,6-trichloropyrido[3,2-d]pyrimidine
1036738-12-1

2,4,6-trichloropyrido[3,2-d]pyrimidine

tert-butyl ((1s,4s)-4-((2,6-dichloropyrido[3,2-d]pyrimidin-4-yl)amino)cyclohexyl)carbamate

tert-butyl ((1s,4s)-4-((2,6-dichloropyrido[3,2-d]pyrimidin-4-yl)amino)cyclohexyl)carbamate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 3h;98%
tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

2-chloronicotinic acid
2942-59-8

2-chloronicotinic acid

syn-{4-[(2-chloro-pyridine-3-carbonyl)-amino]-cyclohexyl}-carbamic acid tert-butyl ester
834868-97-2

syn-{4-[(2-chloro-pyridine-3-carbonyl)-amino]-cyclohexyl}-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: 2-chloronicotinic acid; oxalyl dichloride With N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 3.16667h;
Stage #2: tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate With N-ethyl-N,N-diisopropylamine In dichloromethane for 18h;
97%
tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

3-(5-cyano-1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-indol-3-yl)-3-(m-tolyl)propanoic acid

3-(5-cyano-1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-indol-3-yl)-3-(m-tolyl)propanoic acid

tert-butyl ((1S,4S)-4-(3-(5-cyano-1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-indol-3-yl)-3-(m-tolyl)propanamido)cyclohexyl)carbamate

tert-butyl ((1S,4S)-4-(3-(5-cyano-1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-indol-3-yl)-3-(m-tolyl)propanamido)cyclohexyl)carbamate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃; for 2h; Inert atmosphere;96%
tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

2,4-dichloro-5-bromopyrimidine
36082-50-5

2,4-dichloro-5-bromopyrimidine

tert-butyl ((1S,4S)-4-((5-bromo-2-chloropyrimidin-4-yl)amino)cyclohexyl)carbamate

tert-butyl ((1S,4S)-4-((5-bromo-2-chloropyrimidin-4-yl)amino)cyclohexyl)carbamate

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃;96%
With potassium carbonate In acetonitrile at 0 - 20℃;
tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

2,4-dichloro-2-methylpyrimidine
1780-26-3

2,4-dichloro-2-methylpyrimidine

[cis-4-(6-chloro-2-methyl-pyrimidin-4-ylamino)-cyclohexyl]-carbamic acid tert-butyl ester

[cis-4-(6-chloro-2-methyl-pyrimidin-4-ylamino)-cyclohexyl]-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In methanol Heating / reflux;95%
tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

m-anisoyl chloride
1711-05-3

m-anisoyl chloride

cis-[4-(3-methoxy-benzoylamino)-cyclohexyl]-carbamic acid tert-butyl ester
771543-82-9

cis-[4-(3-methoxy-benzoylamino)-cyclohexyl]-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 1h;94%
tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

2-chloro-N,N-dimethylquinazolin-4-amine
35691-16-8

2-chloro-N,N-dimethylquinazolin-4-amine

tert-butyl (cis-4-{[4-(dimethylamino)quinazolin-2-yl]amino}cyclohexyl)carbamate
509142-47-6

tert-butyl (cis-4-{[4-(dimethylamino)quinazolin-2-yl]amino}cyclohexyl)carbamate

Conditions
ConditionsYield
In isopropyl alcohol for 576h; Heating;93%
In isopropyl alcohol for 168h; Heating;93%
tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

2-[(3,4-difluorophenyl)amino]-5-fluoronicotinic acid
919294-92-1

2-[(3,4-difluorophenyl)amino]-5-fluoronicotinic acid

tert-butyl {cis-4-[({2-[(3,4-difluorophenyl)amino]-5-fluoropyridin-3-yl}carbonyl)amino]cyclohexyl}carbamate

tert-butyl {cis-4-[({2-[(3,4-difluorophenyl)amino]-5-fluoropyridin-3-yl}carbonyl)amino]cyclohexyl}carbamate

Conditions
ConditionsYield
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane for 1h;93%
tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

N-Cbz-L-Phe
1161-13-3

N-Cbz-L-Phe

C28H37N3O5
1094106-67-8

C28H37N3O5

Conditions
ConditionsYield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In tetrahydrofuran at 20℃;91%
tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

1-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-4-methoxy-1H-benzimidazole
1188914-98-8

1-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-4-methoxy-1H-benzimidazole

tert-butyl cis-4-{[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]amino}cyclohexylcarbamate

tert-butyl cis-4-{[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]amino}cyclohexylcarbamate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃;90%
tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

(2-chloro-5,6-dimethyl-pyrimidin-4-yl)-dimethyl-amine

(2-chloro-5,6-dimethyl-pyrimidin-4-yl)-dimethyl-amine

cis-[4-(4-dimethylamino-5,6-dimethyl-pyrimidin-2-ylamino)-cyclohexyl]-carbamic acid tert-butyl ester

cis-[4-(4-dimethylamino-5,6-dimethyl-pyrimidin-2-ylamino)-cyclohexyl]-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 170℃; for 1h;89%
tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

3,4-difluorobenzoyl chloride
76903-88-3

3,4-difluorobenzoyl chloride

(cis-4-{[1-(3,4-difluoro-phenyl)-methanoyl]-amino}-cyclohexyl)-carbamic acid tert-butyl ester
771553-05-0

(cis-4-{[1-(3,4-difluoro-phenyl)-methanoyl]-amino}-cyclohexyl)-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 1h;89%
tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

(2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(o-tolyl)methanone

(2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(o-tolyl)methanone

tert-butyl N-(cis-4-((2-chloro-5-(2-methylbenzoyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)cyclohexyl)carbamate

tert-butyl N-(cis-4-((2-chloro-5-(2-methylbenzoyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)cyclohexyl)carbamate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 160℃; for 1h; Microwave irradiation;89%
tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

2,4-dichloro-6-bromoquinazoline
102393-82-8

2,4-dichloro-6-bromoquinazoline

tert-butyl ((1s,4s)-4-((6-bromo-2-chloroquinazolin-4-yl)amino)cyclohexyl)carbamate

tert-butyl ((1s,4s)-4-((6-bromo-2-chloroquinazolin-4-yl)amino)cyclohexyl)carbamate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 3h;87%
tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

2,4,6-trichloropyrido[3,4-d]pyrimidine

2,4,6-trichloropyrido[3,4-d]pyrimidine

tert-butyl ((1s,4s)-4-((2,6-dichloropyrido[3,4-d]pyrimidin-4-yl)amino)cyclohexyl)carbamate

tert-butyl ((1s,4s)-4-((2,6-dichloropyrido[3,4-d]pyrimidin-4-yl)amino)cyclohexyl)carbamate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 3h;85%
tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

4-(8-bromoquinoxalin-6-yl)morpholine

4-(8-bromoquinoxalin-6-yl)morpholine

tert-butyl (4-((7-morpholinoquinoxalin-5-yl)amino)cyclohexyl)carbamate

tert-butyl (4-((7-morpholinoquinoxalin-5-yl)amino)cyclohexyl)carbamate

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 100℃; for 12h;83.2%
tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

5-fluoro-2-(tetrahydro-2H-thiopyran-4-ylamino)nicotinic acid
950901-74-3

5-fluoro-2-(tetrahydro-2H-thiopyran-4-ylamino)nicotinic acid

tert-butyl [cis-4-({[5-fluoro-2-(tetrahydro-2H-thiopyran-4-ylamino)pyridin-3-yl]carbonyl}amino)cyclohexyl]carbamate
950901-75-4

tert-butyl [cis-4-({[5-fluoro-2-(tetrahydro-2H-thiopyran-4-ylamino)pyridin-3-yl]carbonyl}amino)cyclohexyl]carbamate

Conditions
ConditionsYield
With 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU In 1-methyl-pyrrolidin-2-one at 20℃; for 0.166667h; pH=8 - 9;81%
tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

4-chloro-2-[(E)-2-(4-chlorophenyl)ethenyl]-6-methylquinazoline
1123684-99-0

4-chloro-2-[(E)-2-(4-chlorophenyl)ethenyl]-6-methylquinazoline

tert-butyl cis-[4-((2-[(E)-2-(4-chlorophenyl)ethenyl]-6-methylquinazolin-4-yl)amino)cyclohexyl]carbamate
1123684-92-3

tert-butyl cis-[4-((2-[(E)-2-(4-chlorophenyl)ethenyl]-6-methylquinazolin-4-yl)amino)cyclohexyl]carbamate

Conditions
ConditionsYield
With dmap; triethylamine In toluene for 15h; Reflux;80.6%
tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

chloroacetyl chloride
79-04-9

chloroacetyl chloride

tert-butyl (cis-4-(2-chloroacetamido)cyclohexyl)carbamate

tert-butyl (cis-4-(2-chloroacetamido)cyclohexyl)carbamate

Conditions
ConditionsYield
With triethylamine In dichloromethane at -78 - 20℃;80%
tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

2,6-dichloro-5-methylpyrimidine
1780-31-0

2,6-dichloro-5-methylpyrimidine

cis-[4-(2-chloro-5-methyl-pyrimidin-4-ylamino)-cyclohexyl]-carbamic acid tert-butyl ester

cis-[4-(2-chloro-5-methyl-pyrimidin-4-ylamino)-cyclohexyl]-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 150℃; for 0.25h; microwave field;79%
tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester
5909-24-0

4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester

ethyl 4-(((1S,4S)-4-((tert-butoxycarbonyl)amino)cyclohexyl)amino)-2-(methylthio)pyrimidine-5-carboxylate

ethyl 4-(((1S,4S)-4-((tert-butoxycarbonyl)amino)cyclohexyl)amino)-2-(methylthio)pyrimidine-5-carboxylate

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃;76%
With potassium carbonate In acetonitrile at 20℃;76%
tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

4-chloro-2-(methylsulfanyl)pyrimidine-5-carboxaldehyde
148256-82-0

4-chloro-2-(methylsulfanyl)pyrimidine-5-carboxaldehyde

tert-butyl ((1S,4S)-4-((5-formyl-2-(methylthio)pyrimidin-4-yl)amino)cyclohexyl)carbamate

tert-butyl ((1S,4S)-4-((5-formyl-2-(methylthio)pyrimidin-4-yl)amino)cyclohexyl)carbamate

Conditions
ConditionsYield
In acetonitrile at 20℃;73.2%
tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

2-bromo-5-iodoimidazo[2,1-b][1,3,4]thiadiazole
1246372-52-0

2-bromo-5-iodoimidazo[2,1-b][1,3,4]thiadiazole

(cis)-[4-(5-iodo-imidazo[2,1-b][1,3,4]thiadiazol-2-ylamino)-cyclohexyl]-carbamic acid tert-butyl ester
1360173-85-8

(cis)-[4-(5-iodo-imidazo[2,1-b][1,3,4]thiadiazol-2-ylamino)-cyclohexyl]-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With triethylamine In acetonitrile at 105℃; for 72h;71%
tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

formaldehyd
50-00-0

formaldehyd

tert-butyl (1s,4s)-4-(dimethylamino)cyclohexylcarbamate
1031289-73-2

tert-butyl (1s,4s)-4-(dimethylamino)cyclohexylcarbamate

Conditions
ConditionsYield
With sodium cyanoborohydride In methanol at 20℃;71%
tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate
247570-24-7

tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

6-(4-methoxyphenyl)-1-[2-(morpholin-4-yl)ethyl]-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylic acid

6-(4-methoxyphenyl)-1-[2-(morpholin-4-yl)ethyl]-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylic acid

tert-butyl N-[(1s,4s)-4-[6-(4-methoxyphenyl)-1-[2-(morpholin-4-yl)ethyl]-2-oxo-1,2-dihydro-1,8-naphthyridine-3-amido]cyclohexyl]carbamate

tert-butyl N-[(1s,4s)-4-[6-(4-methoxyphenyl)-1-[2-(morpholin-4-yl)ethyl]-2-oxo-1,2-dihydro-1,8-naphthyridine-3-amido]cyclohexyl]carbamate

Conditions
ConditionsYield
Stage #1: 6-(4-methoxyphenyl)-1-[2-(morpholin-4-yl)ethyl]-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; under 760.051 Torr; for 0.0833333h;
Stage #2: tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; under 760.051 Torr; for 14h;
71%

247570-24-7Relevant articles and documents

INHIBITORS OF BRUTON'S TYROSINE KINASE AND METHODS OF THEIR USE

-

, (2018/06/30)

The present disclosure is directed to compounds of Formula (I) and methods of their use and preparation, as well as compositions comprising compounds of Formula (I).

SELECTIVE KINASE INHIBITORS

-

, (2013/06/06)

Provided are pyrimidine compounds for inhibiting of Syk kinase, intermediates used in making such compounds, methods for their preparation, pharmaceutical compositions thereof, methods for inhibition Syk kinase activity, and methods for treating conditions mediated at least in part by Syk kinase activity.

Crystalline forms of cis-5-fluoro-N-?4-(2-hydroxy-4-methylbenzamido)cyclohexyl|-2-(tetrahydrothiopyran-4-yloxy)nicotinamide

-

Page/Page column 14; 15, (2008/06/13)

The present invention relates to new crystalline forms of syn-5-Fluoro-N-[4-(2-hydroxy-4-methyl-benzoylamino)-cyclohexyl]-2-(tetrahydro-thiopyran-4-yloxy)-nicotinamide and to processes for the preparation of, compositions containing and the uses of such crystalline forms.

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