Conditions | Yield |
---|---|
tetrakis(triphenylphosphine) palladium(0) In toluene at 20℃; for 2h; | 92.3% |
cabergoline
Conditions | Yield |
---|---|
In n-heptane at 55℃; Product distribution / selectivity; | 90% |
at 55 - 70℃; under 1.50015 Torr; for 24 - 92h; Product distribution / selectivity; | |
at 60℃; under 750.075 Torr; for 24h; | |
In diethyl ether; n-heptane at -35 - -15℃; for 8h; Product distribution / selectivity; |
cabergoline
Conditions | Yield |
---|---|
for 15h; Product distribution / selectivity; Drying under a blanket of nitrogen; | 86% |
at 40℃; under 65.2565 - 83.2583 Torr; for 16 - 17h; Product distribution / selectivity; | |
at 60℃; for 20.5h; Product distribution / selectivity; | |
at 20 - 25℃; under 525.053 - 675.068 Torr; for 29.25h; Product distribution / selectivity; Vacuum; | |
at 40℃; for 2h; Product distribution / selectivity; Stream of nitrogen; |
(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
ethyl isocyanate
cabergoline
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 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% |
1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride
(6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylic acid
A
cabergoline
B
N-<<<3-(dimethylamino)propyl>amino>carbonyl>-N-ethyl-6-(2-propenyl)-ergoline-8β-carboxamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 25℃; for 20h; Product distribution / selectivity; | A 54.7% B n/a |
With triethylamine In N,N-dimethyl-formamide Ambient temperature; | A 46% B 35% |
With triethylamine In ethyl acetate at 20℃; Product distribution / selectivity; |
tert-butyl (5R,8R,10R)-6-allyl-8-[[[3-(dimethylamino)propyl][(ethylamino)carbonyl]amino]carbonyl]ergoline-1-carboxylate
cabergoline
Conditions | Yield |
---|---|
With hydrogenchloride In water at 80℃; for 1h; |
methyl (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate
cabergoline
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 85 percent / 2-hydroxypyridine / ethane-1,2-diol / 18 h / 100 °C 2: 92 percent / 4-(dimethylamino)pyridine / tetrahydrofuran / 2 h / 40 °C 3: NaHMDS / tetrahydrofuran / -40 - 20 °C 4: propan-2-ol / 18 h / 50 °C 5: aqueous hydrochloric acid / H2O / 1 h / 80 °C View Scheme | |
Multi-step reaction with 2 steps 1: 85 percent / acetic acid / Heating 2: 81 percent / toluene / Heating 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
cabergoline
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 85 percent / 2-hydroxypyridine / ethane-1,2-diol / 18 h / 100 °C 2: 92 percent / 4-(dimethylamino)pyridine / tetrahydrofuran / 2 h / 40 °C 3: NaHMDS / tetrahydrofuran / -40 - 20 °C 4: propan-2-ol / 18 h / 50 °C 5: aqueous hydrochloric acid / H2O / 1 h / 80 °C View Scheme |
tert-butyl (5R,8R,10R)-6-allyl-8-[[[3-(dimethylamino)propyl]amino]carbonyl]ergoline-1-carboxylate
cabergoline
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: NaHMDS / tetrahydrofuran / -40 - 20 °C 2: propan-2-ol / 18 h / 50 °C 3: aqueous hydrochloric acid / H2O / 1 h / 80 °C View Scheme |
tert-butyl (5R,8R,10R)-6-allyl-8-[[[3-(dimethylamino)propyl](phenoxycarbonyl)amino]carbonyl]ergoline-1-carboxylate
cabergoline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: propan-2-ol / 18 h / 50 °C 2: aqueous hydrochloric acid / H2O / 1 h / 80 °C View Scheme |
1-amino-3-(dimethylamino)propane
cabergoline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 85 percent / acetic acid / Heating 2: 81 percent / toluene / Heating View Scheme |
cabergoline
Conditions | Yield |
---|---|
With ammonium fluoride In tetrahydrofuran; water |
C32H51N5O2Si
cabergoline
Conditions | Yield |
---|---|
With ammonium fluoride In methanol; water at 20℃; for 3h; |
N-(3-dimethylaminopropyl)-N-ethylcarbodiimide
(6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylic acid
cabergoline
Conditions | Yield |
---|---|
Stage #1: N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylic acid In trifluoromethylbenzene (BTF) at 24 - 38℃; Stage #2: With water; acetic acid In trifluoromethylbenzene (BTF) pH=5.0 - 5.5; Stage #3: With potassium hydroxide In tert-butyl methyl ether; water pH=9.5 - 10.0; |
cabergoline
Conditions | Yield |
---|---|
at 30 - 60℃; under 0.750075 Torr; for 25h; Product distribution / selectivity; |
1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride
(6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylic acid
cabergoline
Conditions | Yield |
---|---|
Stage #1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylic acid With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 30h; Stage #2: With ammonia; water In dichloromethane |
Conditions | Yield |
---|---|
Stage #1: tert-Amyl methyl ether; cabergoline at 41 - 50℃; for 0.25h; Stage #2: cabergoline at 0 - 27℃; for 16.5h; | 88.8% |
4-(3-Aminopropyl)morpholine
cabergoline
(5R,8R,10R)-6-allyl-N-[3-(morpholino)propyl]ergoline-8-carboxamide
Conditions | Yield |
---|---|
at 65℃; for 144h; Inert atmosphere; Sealed tube; | 80% |
at 65℃; for 144h; Inert atmosphere; Sealed tube; | 80% |
cabergoline
chlorobenzene
Conditions | Yield |
---|---|
In n-heptane at -20 - 20℃; for 1.25h; |
Conditions | Yield |
---|---|
Stage #1: ethylbenzene; cabergoline at -23 - 30℃; for 0.5h; Stage #2: n-heptane at -23 - -17℃; for 3.66667h; |
methanol
cabergoline
methyl (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate
Conditions | Yield |
---|---|
With triethylamine |
cabergoline
(5R,8R,10R)-6-allyl-N-[3-(morpholino)propyl]-N-[(ethylamino)carbonyl]-ergoline-8-carboxamide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide / water; methanol 2: triethylamine / dichloromethane View Scheme | |
Multi-step reaction with 3 steps 1: 144 h / 65 °C / Inert atmosphere; Sealed tube 2: dmap / tetrahydrofuran 3: isopropyl alcohol / 50 °C View Scheme |
cabergoline
(6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylic acid
Conditions | Yield |
---|---|
Stage #1: cabergoline With sodium hydroxide In methanol; water Stage #2: With hydrogenchloride In methanol; water |
cabergoline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 144 h / 65 °C / Inert atmosphere; Sealed tube 2: dmap / tetrahydrofuran View Scheme |
Conditions | Yield |
---|---|
With copper (I) acetate In methanol at 40℃; for 4.5h; Inert atmosphere; |
Conditions | Yield |
---|---|
Stage #1: cabergoline; β‐cyclodextrin In methanol; water at 20℃; for 0.5h; Sonication; Stage #2: In methanol; water at 20 - 50℃; for 48h; |
N-ethyl-L-glutamine
cabergoline
Conditions | Yield |
---|---|
In water; isopropyl alcohol |
Molecular Structure of Cabergoline (CAS NO.81409-90-7):
Molecular Formula: C26H37N5O2
Formula Weight: 451.6
H bond acceptors: 7
H bond donors: 2
Freely Rotating Bonds: 8
Polar Surface Area: 71.68 Å2
Index of Refraction: 1.594
Molar Refractivity: 132.54 cm3
Molar Volume: 390.4 cm3
Surface Tension: 48.6 dyne/cm
Density: 1.156 g/cm3
Melting point: 102-104°C
InChI
InChI=1/C26H37N5O2/c1-5-11-30-17-19(25(32)31(26(33)27-6-2)13-8-12-29(3)4)14-21-20-9-7-10-22-24(20)18(16-28-22)15-23(21)30/h5,7,9-10,16,19,21,23,28H,1,6,8,11-15,17H2,2-4H3,(H,27,33)/t19-,21-,23-/m1/s1
Smiles
c12[C@@H]3[C@H]([N@@](C[C@@H](C3)C(N(C(NCC)=O)CCCN(C)C)=O)CC=C)Cc3c1c([nH]c3)ccc2
Product Categories: Intermediates & Fine Chemicals; Neurochemicals; Pharmaceuticals
Cabergoline was invented by scientists working for the Italian drug company Farmitalia-Carlo Erba SpA in Milan in 1981/82, who were experimenting with semisynthetic derivatives of the ergot alkaloids. Farmitalia-Carlo Erba was acquired by Pharmacia in 1992, which in turn was acquired by Pfizer in 2002. The drug was not FDA approved until 2002. It went generic in late 2005 following US patent expiration.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | oral | > 400mg/kg (400mg/kg) | European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 24, Pg. 421, 1989. |
Cabergoline , with CAS number of 81409-90-7, can be called Ergoline-8-carboxamide,N-[3-(dimethylamino)propyl]-N-[(ethylamino)carbonyl]-6-(2-propenyl)-, (8b)- (9CI) ; Cabaser ; Cabaseril ; 1-((6-Allylergolin-8beta-yl)carbonyl)-1-(3-(dimethylamino)propyl)-3-ethylurea ; Ergoline-8beta-carboxamide, N-(3-(dimethylamino)propyl)-N-((ethylamino)carbonyl)-6-(2-propenyl)- . It is a white crystalline solid, used as a dopamine D2-receptor agonist. It is frequently used as a second-line agent in the management of prolactinomas when bromocriptine is ineffective.
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