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 cyclopropylamide hydrochloride

HRID 221457Notes

Reaction equation

HRID 221457 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH2:31][C:32]1[CH:37]=[C:36]([F:38])[C:35]([F:39])=[CH:34][C:33]=1[F:40])[CH2:9][C:10]([N:12]1[CH2:17][CH2:16][N:15]2[C:18]([C:27]([F:30])([F:29])[F:28])=[N:19][C:20]([C:21](=[O:26])[NH:22][CH:23]3[CH2:25][CH2:24]3)=[C:14]2[CH2:13]1)=[O:11])(C)(C)C.[ClH:42]>C(OCC)(=O)C>[ClH:42].[CH:23]1([NH:22][C:21]([C:20]2[N:19]=[C:18]([C:27]([F:28])([F:30])[F:29])[N:15]3[CH2:16][CH2:17][N:12]([C:10](=[O:11])[CH2:9][C@H:8]([NH2:7])[CH2:31][C:32]4[CH:37]=[C:36]([F:38])[C:35]([F:39])=[CH:34][C:33]=4[F:40])[CH2:13][C:14]=23)=[O:26])[CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57518431HCID 57518431, compound

Product 1

HCID 44194132(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 cyclopropylamide hydrochlorideYield 95%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(R)-[3-(1-Cyclopropylcarbamoyl-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 15a (0.1 g, 0.16 mmol) was added to a solution of 2.2 N hydrochloric acid in 5 mL of ethyl acetate. The reaction mixture was reacted at room temperature overnight 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 cyclopropylamide hydrochloride 15 (82 mg, yield 95%) as a light yellow solid.

Workup

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

Sources & evidence

ORD record
ord-bf1e4e79c1d146ddbaa74a6dcc3f6c76
Source dataset
uspto-grants-2012_06
Patent number
US08207161B2

Reaction notes

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