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CAS No.: | 85329-86-8 |
---|---|
Name: | Desethylcarbamoyl Cabergoline |
Article Data: | 3 |
Molecular Structure: | |
Formula: | C23H32N4O |
Molecular Weight: | 380.533 |
Synonyms: | Cabergoline specified impurity D;Cabergoline related compound D;Desethylcarbamoyl Cabergoline;UNII-114UFJ65CL; |
Density: | 1.13g/cm3 |
Melting Point: | 188-190°C |
Boiling Point: | 607.7°C at 760 mmHg |
Flash Point: | 321.3°C |
PSA: | 54.86000 |
LogP: | 3.53020 |
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
(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 | Yield |
---|---|
In acetic acid Heating; | 85% |
With 2-hydroxypyridin In ethylene glycol at 100℃; for 18h; | 85% |
With acetic acid for 24h; Reflux; | 74% |
9,10-dihydrolysergic acid methyl ester
(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 | Yield |
---|---|
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
(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 | Yield |
---|---|
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
(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 | Yield |
---|---|
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
(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 | Yield |
---|---|
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
(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 | Yield |
---|---|
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
(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
Conditions | Yield |
---|---|
With dmap In tetrahydrofuran at 40℃; for 2h; | 92% |
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
Conditions | Yield |
---|---|
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
ethyl isocyanate
A
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
Conditions | Yield |
---|---|
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
methyl isocyanate
N-<3-(dimethylamino)propyl>-N-<(methylamino)-carbonyl>-6-(2-propenyl)-ergoline-8β-carboxamide
Conditions | Yield |
---|---|
80% |