(S)-2-(Methylamino)-2-oxo-1-phenylethyl 4-methylbenzenesulfonate → 3-Ethyl-7-(methylcarbamoyl-phenyl-methyl)-8-[2-(4-trifluoromethyl-phenyl)-ethyl]-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid methylamide

HRID 1929723Notes

Reaction equation

HRID 1929723 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[N:6]=[C:7]([CH2:26][CH3:27])[N:8]2[CH2:13][CH2:12][NH:11][CH:10]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)[C:9]=12)=[O:4].[CH3:28][NH:29][C:30]([C@@H:32](OS(C1C=CC(C)=CC=1)(=O)=O)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:31]>>[CH3:1][NH:2][C:3]([C:5]1[N:6]=[C:7]([CH2:26][CH3:27])[N:8]2[CH2:13][CH2:12][N:11]([CH:32]([C:30](=[O:31])[NH:29][CH3:28])[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH:10]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)[C:9]=12)=[O:4]

Participants

3

Reactant 2

HCID 57354974(S)-2-(Methylamino)-2-oxo-1-phenylethyl 4-methylbenzenesulfonateHCID 667342233-Ethyl-8-[2-(4-trifluoromethyl-phenyl)-ethyl]-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid methylamide

Product 1

HCID 667338563-Ethyl-7-(methylcarbamoyl-phenyl-methyl)-8-[2-(4-trifluoromethyl-phenyl)-ethyl]-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid methylamide

Procedure

Prepared by reaction of 3-ethyl-8-[2-(4-trifluoromethyl-phenyl)-ethyl]-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid methylamide (22 mg; 0.057 mmol) with toluene-4-sulfonic acid (S)-methylcarbamoyl-phenyl-methyl ester. Purification by preparative HPLC afforded the mixture of 2 diastereoisomers. LC-MS: tR=0.86 min., [M+H]+=528.45 g/mol.

Workup

  1. customPurification by preparative HPLC
  2. customafforded
  3. additionthe mixture of 2 diastereoisomers

Sources & evidence

ORD record
ord-b0c79b29a24947b19d64dedfdfbea1fc
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

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