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85329-86-8 Usage

Chemical Properties

Tan Solid

Uses

A metabolite of Cabergoline, having affinity for D1 and D2 dopamine receptors in rat striatum

Check Digit Verification of cas no

The CAS Registry Mumber 85329-86-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,5,3,2 and 9 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 85329-86:
(7*8)+(6*5)+(5*3)+(4*2)+(3*9)+(2*8)+(1*6)=158
158 % 10 = 8
So 85329-86-8 is a valid CAS Registry Number.
InChI:InChI=1/C23H32N4O/c1-4-10-27-15-17(23(28)24-9-6-11-26(2)3)12-19-18-7-5-8-20-22(18)16(14-25-20)13-21(19)27/h4-5,7-8,14,17,19,21,25H,1,6,9-13,15H2,2-3H3,(H,24,28)/t17-,19?,21-/m1/s1

85329-86-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name (6aR,9R,10aR)-N-[3-(dimethylamino)propyl]-7-prop-2-enyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide

1.2 Other means of identification

Product number -
Other names Desethylcarbamoyl Cabergoline

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:85329-86-8 SDS

85329-86-8Synthetic route

methyl (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate
72821-79-5

methyl (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate

1-amino-3-(dimethylamino)propane
109-55-7

1-amino-3-(dimethylamino)propane

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide
85329-86-8

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

Conditions
ConditionsYield
In acetic acid Heating;85%
With 2-hydroxypyridin In ethylene glycol at 100℃; for 18h;85%
With acetic acid for 24h; Reflux;74%
(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide
85329-86-8

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: dmap / dichloromethane / 16 h / Reflux; Inert atmosphere
2: zinc / methanol; acetic acid / 1.08 h / 20 °C
3: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 35 °C
4: acetic acid / 24 h / Reflux
View Scheme
9-methyl 7-(2,2,2-trichloroethyl) (6aR,9R,10aR)-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-7,9(4H)-dicarboxylate
80993-64-2

9-methyl 7-(2,2,2-trichloroethyl) (6aR,9R,10aR)-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-7,9(4H)-dicarboxylate

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide
85329-86-8

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: zinc / methanol; acetic acid / 1.08 h / 20 °C
2: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 35 °C
3: acetic acid / 24 h / Reflux
View Scheme
methyl (6aR,9R,10aR)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate
30341-92-5

methyl (6aR,9R,10aR)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide
85329-86-8

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 35 °C
2: acetic acid / 24 h / Reflux
View Scheme
Dihydroergocryptine
25447-66-9

Dihydroergocryptine

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide
85329-86-8

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: sodium hydroxide; sodium dithionite / water / 4 h / Reflux
2: sulfuric acid / 15 h / 20 °C
3: dmap / dichloromethane / 16 h / Reflux; Inert atmosphere
4: zinc / methanol; acetic acid / 1.08 h / 20 °C
5: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 35 °C
6: acetic acid / 24 h / Reflux
View Scheme
9,10-dihydrolysergic acid
5878-43-3

9,10-dihydrolysergic acid

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide
85329-86-8

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sulfuric acid / 15 h / 20 °C
2: dmap / dichloromethane / 16 h / Reflux; Inert atmosphere
3: zinc / methanol; acetic acid / 1.08 h / 20 °C
4: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 35 °C
5: acetic acid / 24 h / Reflux
View Scheme
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide
85329-86-8

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

tert-butyl (5R,8R,10R)-6-allyl-8-[[[3-(dimethylamino)propyl]amino]carbonyl]ergoline-1-carboxylate
474397-67-6

tert-butyl (5R,8R,10R)-6-allyl-8-[[[3-(dimethylamino)propyl]amino]carbonyl]ergoline-1-carboxylate

Conditions
ConditionsYield
With dmap In tetrahydrofuran at 40℃; for 2h;92%
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide
85329-86-8

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

C29H46N4OSi

C29H46N4OSi

Conditions
ConditionsYield
Stage #1: (6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide With sodium hydride In tetrahydrofuran at 20℃; for 1.5h;
Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran at 20℃; for 1.25h;
86.5%
(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide
85329-86-8

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

ethyl isocyanate
109-90-0

ethyl isocyanate

A

cabergoline
81409-90-7

cabergoline

B

(6aR,9R,10aR)-7-allyl-N9-[3-(dimethylamino)propyl]-N4-ethyl-N9-(ethylcarbamoyl)-6a,7,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-4,9(6H)-dicarboxamide
126554-50-5

(6aR,9R,10aR)-7-allyl-N9-[3-(dimethylamino)propyl]-N4-ethyl-N9-(ethylcarbamoyl)-6a,7,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-4,9(6H)-dicarboxamide

Conditions
ConditionsYield
In toluene Heating;A 81%
B 0.57 g
(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide
85329-86-8

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

methyl isocyanate
624-83-9

methyl isocyanate

N-<3-(dimethylamino)propyl>-N-<(methylamino)-carbonyl>-6-(2-propenyl)-ergoline-8β-carboxamide
126554-48-1

N-<3-(dimethylamino)propyl>-N-<(methylamino)-carbonyl>-6-(2-propenyl)-ergoline-8β-carboxamide

Conditions
ConditionsYield
80%
phenyl isocyanate
103-71-9

phenyl isocyanate

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide
85329-86-8

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

N-<3-(dimethylamino)propyl>-N-<(phenylamino)-carbonyl>-6-(2-propenyl)-ergoline-8β-carboxamide
126554-49-2

N-<3-(dimethylamino)propyl>-N-<(phenylamino)-carbonyl>-6-(2-propenyl)-ergoline-8β-carboxamide

Conditions
ConditionsYield
74%
(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide
85329-86-8

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

ethyl isocyanate
109-90-0

ethyl isocyanate

cabergoline
81409-90-7

cabergoline

Conditions
ConditionsYield
Stage #1: (6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide With trimethylsilyl trifluoromethanesulfonate; triethylamine In dichloromethane at -2 - 18℃; for 14h;
Stage #2: ethyl isocyanate In dichloromethane at 18℃; for 48h;
Stage #3: With tetrabutyl ammonium fluoride In tetrahydrofuran; dichloromethane at -2℃; for 4h;
68.2%
(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide
85329-86-8

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

cabergoline
81409-90-7

cabergoline

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 92 percent / 4-(dimethylamino)pyridine / tetrahydrofuran / 2 h / 40 °C
2: NaHMDS / tetrahydrofuran / -40 - 20 °C
3: propan-2-ol / 18 h / 50 °C
4: aqueous hydrochloric acid / H2O / 1 h / 80 °C
View Scheme
(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide
85329-86-8

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

7-allyl-9-ethylcarbamoyl-6a,7,8,9,10,10a-hexahydro-6H-indolo[4,3-fg]quinoline-4-carboxylic acid tert-butyl ester

7-allyl-9-ethylcarbamoyl-6a,7,8,9,10,10a-hexahydro-6H-indolo[4,3-fg]quinoline-4-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 92 percent / 4-(dimethylamino)pyridine / tetrahydrofuran / 2 h / 40 °C
2: NaHMDS / tetrahydrofuran / -40 - 20 °C
3: propan-2-ol / 18 h / 50 °C
View Scheme
(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide
85329-86-8

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

tert-butyl (5R,8R,10R)-6-allyl-8-[[[3-(dimethylamino)propyl][(ethylamino)carbonyl]amino]carbonyl]ergoline-1-carboxylate
474397-69-8

tert-butyl (5R,8R,10R)-6-allyl-8-[[[3-(dimethylamino)propyl][(ethylamino)carbonyl]amino]carbonyl]ergoline-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 92 percent / 4-(dimethylamino)pyridine / tetrahydrofuran / 2 h / 40 °C
2: NaHMDS / tetrahydrofuran / -40 - 20 °C
3: propan-2-ol / 18 h / 50 °C
View Scheme
(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide
85329-86-8

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

tert-butyl (5R,8R,10R)-6-allyl-8-[[[3-(dimethylamino)propyl](phenoxycarbonyl)amino]carbonyl]ergoline-1-carboxylate
474397-68-7

tert-butyl (5R,8R,10R)-6-allyl-8-[[[3-(dimethylamino)propyl](phenoxycarbonyl)amino]carbonyl]ergoline-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 92 percent / 4-(dimethylamino)pyridine / tetrahydrofuran / 2 h / 40 °C
2: NaHMDS / tetrahydrofuran / -40 - 20 °C
View Scheme
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide
85329-86-8

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

C26H40N4OSi

C26H40N4OSi

Conditions
ConditionsYield
Stage #1: (6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide With sodium hydride In tetrahydrofuran at 20 - 45℃; for 1h;
Stage #2: chloro-trimethyl-silane In tetrahydrofuran at 20℃; for 1h;

85329-86-8Relevant articles and documents

Synthesis of European pharmacopoeial impurities A, B, C, and D of cabergoline

Wagger, Jernej,Pozes, Aljaz,Pozgan, Franc

, p. 23146 - 23156 (2013/11/19)

For the use of analytics, European pharmacopoeial impurities A, B, C, and D of cabergoline were synthesized. Ergocryptine was chosen as a starting material and synthesis was accomplished via two approaches, different in length and stereochemical outcome. A longer, indirect approach was realized through otherwise problematic oxidations of the 9,10-dihidrolysergol derivative, to the corresponding aldehyde and carboxylic acid. This was achieved by the use of activated DMSO and a Pinnick oxidation sequence. All four synthesized impurities are used as analytical standards in cabergoline manufacturing processes.

Synthesis and nidation inhibitory activity of a new class of ergoline derivatives

Brambilla,Disalle,Briatico,Mantegani,Temperilli

, p. 421 - 426 (2007/10/02)

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