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-carbonyl}-amino)-acetic acid methyl ester hydrochloride

HRID 1895617Notes

Reaction equation

HRID 1895617 reaction equation
[CH3:1][O:2][C:3](=[O:43])[CH2:4][NH:5][C:6]([C:8]1[N:9]=[C:10]([C:39]([F:42])([F:41])[F:40])[N:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:38])[CH2:18][C@H:19]([NH:30]C(OC(C)(C)C)=O)[CH2:20][C:21]3[CH:26]=[C:25]([F:27])[C:24]([F:28])=[CH:23][C:22]=3[F:29])[CH2:13][C:12]=12)=[O:7].[ClH:44]>C(OCC)(=O)C>[ClH:44].[CH3:1][O:2][C:3](=[O:43])[CH2:4][NH:5][C:6]([C:8]1[N:9]=[C:10]([C:39]([F:41])([F:40])[F:42])[N:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:38])[CH2:18][C@H:19]([NH2:30])[CH2:20][C:21]3[CH:26]=[C:25]([F:27])[C:24]([F:28])=[CH:23][C:22]=3[F:29])[CH2:13][C:12]=12)=[O:7]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59548956HCID 59548956, compound

Product 1

HCID 44194134(R)-({7-[3-Amino-4-(2,4,5-trifluoro-phenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carbonyl}-amino)-acetic acid methyl ester hydrochlorideYield 99%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

(R)-({7-[3-tert-Butoxycarbonylamino-4-(2,4,5-trifluoro-phenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carbonyl}-amino)-acetic acid methyl ester 16a (0.09 g, 0.145 mmol) and 2 mL of ethyl acetate were added into the reaction flask. A solution of 2.3 N hydrochloric acid in 4 mL of ethyl acetate was then added to the flask. The reaction mixture was reacted at room temperature for 3 hours 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-carbonyl}-amino)-acetic acid methyl ester hydrochloride 16 (80 mg, yield 99%) as a white solid.

Workup

  1. customThe reaction mixture was reacted at room temperature for 3 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2b0db1fd1e10477084a670526a2f1773
Source dataset
uspto-grants-2013_08
Patent number
US08513411B2

Reaction notes

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