Trifluoroacetic acid → HCID 44194617, compound

HRID 221516Notes

Reaction equation

HRID 221516 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][CH:16](C(=O)N)[N:15]2[C:21]([C:27]([F:30])([F:29])[F:28])=[N:22][C:23](CCC)=[C:14]2[CH2:13]1)=[O:11])(C)(C)C.FC(F)(F)[C:44]([OH:46])=O>ClCCl>[CH2:8]([NH:7][C:44]([C:23]1[N:22]=[C:21]([C:27]([F:30])([F:29])[F:28])[N:15]2[CH2:16][CH2:17][N:12]([C:10](=[O:11])[CH2:9][C@H:8]([NH2:7])[CH2:31][C:32]3[CH:37]=[C:36]([F:38])[C:35]([F:39])=[CH:34][C:33]=3[F:40])[CH2:13][C:14]=12)=[O:46])[CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86646930HCID 86646930, compound

Product 1

HCID 44194617HCID 44194617, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-[3-(1-Propylcarbamoyl-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 44a (70 mg, 0.118 mmol) was dissolved in 10 mL of dichloromethane, and trifluoroacetic acid (270 mg, 2.37 mmol) was then added to the solution. The reaction mixture was stirred at room temperature for 1 hour 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)-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 propylamide 44 (25 mg, yield 43.1%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f8fea191d57a44b895c534bc1933aafe
Source dataset
uspto-grants-2012_06
Patent number
US08207161B2

Reaction notes

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