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

HRID 1895671Notes

Reaction equation

HRID 1895671 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([C:37]([F:40])([F:39])[F:38])[N:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:35])[CH2:15][CH:16]([NH:27]C(OC(C)(C)C)=O)[CH2:17][C:18]3[CH:23]=[C:22]([F:24])[C:21]([F:25])=[CH:20][C:19]=3[F:26])[C@H:10]([CH3:36])[C:9]=12)=[O:4].[ClH:41]>C(OCC)(=O)C>[ClH:41].[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([C:37]([F:40])([F:38])[F:39])[N:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:35])[CH2:15][CH:16]([NH2:27])[CH2:17][C:18]3[CH:23]=[C:22]([F:24])[C:21]([F:25])=[CH:20][C:19]=3[F:26])[C@H:10]([CH3:36])[C:9]=12)=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57518482(R)-7-[3-tert-Butoxycarbonylamino-4-(2,4,5-trifluoro-phenyl)-butyryl]-8-methyl-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid methyl ester

Product 1

HCID 86646929(R)-7-[3-amino-4-(2,4,5-trifluoro-phenyl)-butyryl]-8-methyl-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid methyl ester hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(R)-7-[3-tert-Butoxycarbonylamino-4-(2,4,5-trifluoro-phenyl)-butyryl]-8-methyl-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid methyl ester 39d (0.23 g, 0.4 mmol) was 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 stirred at room temperature for 2 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]-8-methyl-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid methyl ester hydrochloride 39 (0.205 g, yield 100%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4e3e19004e6649c69cb91d61492ba191
Source dataset
uspto-grants-2013_08
Patent number
US08513411B2

Reaction notes

Loading…