Hydrochloric Acid → 8-Methyl-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid methyl ester hydrochloride

HRID 221508Notes

Reaction equation

HRID 221508 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([C:22]([F:25])([F:24])[F:23])[N:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH:10]([CH3:21])[C:9]=12)=[O:4].[ClH:26]>C(OCC)(=O)C>[ClH:26].[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([C:22]([F:25])([F:24])[F:23])[N:8]2[CH2:13][CH2:12][NH:11][CH:10]([CH3:21])[C:9]=12)=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 575184808-methyl-3-trifluoromethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-1,7-dicarboxylic acid 7-tert-butyl ester 1-methyl ester

Product 1

HCID 684212988-Methyl-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid methyl ester hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

8-Methyl-3-trifluoromethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-1,7-dicarboxylic acid 7-tert-butyl ester 1-methyl ester 39b (0.35 g, 0.96 mmol) was added into the reaction flask. A solution of 2.3 N hydrochloric acid in 10 mL of ethyl acetate was then added to the flask. 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 to obtain the title compound 8-methyl-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid methyl ester hydrochloride 39c crude product (0.4 g) as a yellow oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-55b2dc6ccb2a48fe86e0c4b7676de441
Source dataset
uspto-grants-2012_06
Patent number
US08207161B2

Reaction notes

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