Hydrochloric Acid → (R)-7-[3-amino-4-(2,4,5-trifluoro-phenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid methylamide hydrochloride

HRID 1895602Notes

Reaction equation

HRID 1895602 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH2:29][C:30]1[CH:35]=[C:34]([F:36])[C:33]([F:37])=[CH:32][C:31]=1[F:38])[CH2:9][C:10]([N:12]1[CH2:17][CH2:16][N:15]2[C:18]([C:25]([F:28])([F:27])[F:26])=[N:19][C:20]([C:21](=[O:24])[NH:22][CH3:23])=[C:14]2[CH2:13]1)=[O:11])(C)(C)C.[ClH:40]>C(OCC)(=O)C>[ClH:40].[CH3:23][NH:22][C:21]([C:20]1[N:19]=[C:18]([C:25]([F:28])([F:26])[F:27])[N:15]2[CH2:16][CH2:17][N:12]([C:10](=[O:11])[CH2:9][C@H:8]([NH2:7])[CH2:29][C:30]3[CH:35]=[C:34]([F:36])[C:33]([F:37])=[CH:32][C:31]=3[F:38])[CH2:13][C:14]=12)=[O:24]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57518418(R)-[3-(1-methylcarbamoyl-3-trifluoromethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazin-7-yl)-3-oxo-1-(2,4,5-trifluoro-benzyl)-propyl]-carbamic acid tert-butyl ester

Product 1

HCID 44193940(R)-7-[3-amino-4-(2,4,5-trifluoro-phenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid methylamide hydrochlorideYield 90%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

(R)-[3-(1-Methylcarbamoyl-3-trifluoromethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazin-7-yl)-3-oxo-1-(2,4,5-trifluoro-benzyl)-propyl]-carbamic acid tert-butyl ester 8a (0.15 g, 0.27 mmol) and 2 mL of ethyl acetate were added into the reaction flask. A solution of 2.3 N hydrochloric acid in 5 mL of ethyl acetate was then added to the flask. The reaction mixture was reacted at room temperature for 4 hours and monitored by thin layer chromatography until the disappearance of the starting materials. The reaction mixture was concentrated under reduced pressure to obtain the title compound (R)-7-[3-amino-4-(2,4,5-trifluoro-phenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid methylamide hydrochloride 8 (0.135 g, yield 90%) as a white solid.

Workup

  1. customThe reaction mixture was reacted at room temperature for 4 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-25c59df1b5ac487cb5d105b2e926674e
Source dataset
uspto-grants-2013_08
Patent number
US08513411B2

Reaction notes

Loading…