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 1895615Notes

Reaction equation

HRID 1895615 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-0f5d8086cef9495a96a2a88265754de6
Source dataset
uspto-grants-2013_08
Patent number
US08513411B2

Reaction notes

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