Hydrochloric Acid → (R)-3-amino-1-[1-(thiazolidine-3-carbonyl)-3-trifluoromethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazin-7-yl]-4-(2,4,5-trifluoro-phenyl)-butan-1-one hydrochloride

HRID 1895624Notes

Reaction equation

HRID 1895624 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH2:32][C:33]1[CH:38]=[C:37]([F:39])[C:36]([F:40])=[CH:35][C:34]=1[F:41])[CH2:9][C:10](=[O:31])[N:11]1[CH2:16][CH2:15][N:14]2[C:17]([C:27]([F:30])([F:29])[F:28])=[N:18][C:19]([C:20]([N:22]3[CH2:26][CH2:25][S:24][CH2:23]3)=[O:21])=[C:13]2[CH2:12]1)(C)(C)C.[ClH:43]>C(OCC)(=O)C>[ClH:43].[NH2:7][C@H:8]([CH2:32][C:33]1[CH:38]=[C:37]([F:39])[C:36]([F:40])=[CH:35][C:34]=1[F:41])[CH2:9][C:10]([N:11]1[CH2:16][CH2:15][N:14]2[C:17]([C:27]([F:28])([F:30])[F:29])=[N:18][C:19]([C:20]([N:22]3[CH2:26][CH2:25][S:24][CH2:23]3)=[O:21])=[C:13]2[CH2:12]1)=[O:31]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57518440HCID 57518440, compound

Product 1

HCID 44194227(R)-3-amino-1-[1-(thiazolidine-3-carbonyl)-3-trifluoromethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazin-7-yl]-4-(2,4,5-trifluoro-phenyl)-butan-1-one hydrochlorideYield 75%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(R)-[3-Oxo-3-[1-(thiazolidine-3-carbonyl)-3-trifluoromethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazin-7-yl]-1-(2,4,5-trifluoro-benzyl)-propyl]-carbamic acid tert-butyl ester 20a (0.15 g, 0.24 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 for 4 hours and monitored by thin layer chromatography until the disappearance of the starting materials. The reaction mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (R)-3-amino-1-[1-(thiazolidine-3-carbonyl)-3-trifluoromethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazin-7-yl]-4-(2,4,5-trifluoro-phenyl)-butan-1-one hydrochloride 20 (100 mg, yield 75%) as a light yellow solid.

Workup

  1. customThe reaction mixture was reacted at room temperature for 4 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d1a2b3d8a5d647d3b30f955a482f604d
Source dataset
uspto-grants-2013_08
Patent number
US08513411B2

Reaction notes

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