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 dimethylamide hydrochloride

HRID 1895604Notes

Reaction equation

HRID 1895604 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH2:30][C:31]1[CH:36]=[C:35]([F:37])[C:34]([F:38])=[CH:33][C:32]=1[F:39])[CH2:9][C:10]([N:12]1[CH2:17][CH2:16][N:15]2[C:18]([C:26]([F:29])([F:28])[F:27])=[N:19][C:20]([C:21](=[O:25])[N:22]([CH3:24])[CH3:23])=[C:14]2[CH2:13]1)=[O:11])(C)(C)C.[ClH:41]>C(OCC)(=O)C>[ClH:41].[CH3:24][N:22]([CH3:23])[C:21]([C:20]1[N:19]=[C:18]([C:26]([F:29])([F:27])[F:28])[N:15]2[CH2:16][CH2:17][N:12]([C:10](=[O:11])[CH2:9][C@H:8]([NH2:7])[CH2:30][C:31]3[CH:36]=[C:35]([F:37])[C:34]([F:38])=[CH:33][C:32]=3[F:39])[CH2:13][C:14]=12)=[O:25]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57518420HCID 57518420, compound

Product 1

HCID 44193942(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 dimethylamide hydrochlorideYield 98%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

(R)-[3-(1-Dimethylcarbamoyl-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 9a (0.138 g, 0.245 mmol) and 2 mL of ethyl acetate were added into the reaction flask. A solution of 2.3 N hydrochloric acid in 4 mL of ethyl acetate was then added to the flask. The reaction mixture was reacted at room temperature for 3 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 dimethylamide hydrochloride 9 (0.12 g, yield 98%) as a white solid.

Workup

  1. customThe reaction mixture was reacted at room temperature for 3 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e6a6998ab1194505936eab4deb108216
Source dataset
uspto-grants-2013_08
Patent number
US08513411B2

Reaction notes

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