Trifluoroacetic acid → HCID 59548955, compound

HRID 1895673Notes

Reaction equation

HRID 1895673 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])[NH:22][CH2:23][CH3:24])=[C:14]2[CH2:13]1)=[O:11])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:23]([NH:22][C:21]([C:20]1[N:19]=[C:18]([C:26]([F:28])([F:29])[F:27])[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])[CH3:24]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57518484HCID 57518484, compound

Product 1

HCID 59548955HCID 59548955, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-[3-(1-Ethylcarbamoyl-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 42a (190 mg, 0.33 mmol) was dissolved in 10 mL of dichloromethane, and trifluoroacetic acid (750 mg, 6.6 mmol) was added to the solution. The reaction mixture was stirred at room temperature for 2 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)-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 ethylamide 42 (120 mg, yield 76.4%) 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-e9564964f71849888111ec8b0ae8749e
Source dataset
uspto-grants-2013_08
Patent number
US08513411B2

Reaction notes

Loading…