Dichloromethane → (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 cyanomethyl-amide hydrochloride

HRID 1895594Notes

Reaction equation

HRID 1895594 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][CH2:23][C:24]#[N:25])=[C:14]2[CH2:13]1)=[O:11])(C)(C)C.FC(F)(F)C(O)=O.[Cl:49]CCl>>[ClH:49].[C:24]([CH2:23][NH:22][C:21]([C:20]1[N:19]=[C:18]([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:26])#[N:25]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 57518409(R)-[3-[1-(cyanomethyl-carbamoyl)-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

Product 1

HCID 44193835(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 cyanomethyl-amide hydrochloride

Procedure

(R)-[3-[1-(Cyanomethyl-carbamoyl)-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 4a (0.3 g, 0.25 mmol) was dissolved in 10 mL of dichloromethane, and 5 mL of trifluoroacetic acid was then added to the solution. The reaction mixture was reacted at room temperature for 1 hour until thin lay chromatography showed the starting material disappeared. 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 cyanomethyl-amide hydrochloride 4 (130 mg) as a light yellow solid.

Workup

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

Sources & evidence

ORD record
ord-4b31ba599d0d49b6b553eb836a167f38
Source dataset
uspto-grants-2013_08
Patent number
US08513411B2

Reaction notes

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