Cabergoline → HCID 69068522, compound

HRID 2087082Notes

Reaction equation

HRID 2087082 reaction equation
[CH3:1][CH2:2][NH:3][C:4]([N:6]([C:13]([C@H:15]1[CH2:30][N:29]([CH2:31][CH:32]=[CH2:33])[C@H:28]2[C@@H:17]([C:18]3[C:23]4[C:24]([CH2:27]2)=[CH:25][NH:26][C:22]=4[CH:21]=[CH:20][CH:19]=3)[CH2:16]1)=[O:14])[CH2:7][CH2:8][CH2:9][N:10]([CH3:12])[CH3:11])=[O:5]>C1(C)C=CC=CC=1>[CH3:1][CH2:2][NH:3][C:4]([N:6]([C:13]([C@H:15]1[CH2:30][N:29]([CH2:31][CH:32]=[CH2:33])[C@H:28]2[C@@H:17]([C:18]3[C:23]4[C:24]([CH2:27]2)=[CH:25][NH:26][C:22]=4[CH:21]=[CH:20][CH:19]=3)[CH2:16]1)=[O:14])[CH2:7][CH2:8][CH2:9][N:10]([CH3:12])[CH3:11])=[O:5].[C:17]1([CH3:16])[CH:28]=[CH:27][CH:24]=[CH:23][CH:18]=1

Participants

3

Reactant 1

HCID 54746Cabergoline

Product 1

HCID 69068522HCID 69068522, compoundYield 403.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The oil obtained by purification on a chromatographic column after the final step of the synthetic path according to the preparation described in Eur. J. Med. Chem., 24, 421, (1989) and containing 100 g of pure cabergoline was dissolved in toluene to give 243 g of a cabergoline toluene solution. The solution was introduced into a reactor pre-cooled at −12° C., and 182 g of toluene were added to give a 23.5%. w/w cabergoline concentration in this solvent. After cooling again at −12° C., 362 ml of diethyl ether were added. The mixture was cooled again at −12° C. and stirred at this temperature for about 17 hours. The obtained precipitate was filtered under vacuum and smoothly dried. The resultant crystal solvate form V was identified by XRD, DSC, IR and NMR, data shown in FIGS. 5-8 respectively.

Workup

  1. customThe oil obtained by purification on a chromatographic column after the final step of the synthetic path

Sources & evidence

ORD record
ord-eda90de97333469582864d5d4db451f5
Source dataset
uspto-grants-2004_04
Patent number
US06727363B2

Reaction notes

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