Triethylamine → (R)-3-(4-isopropyl-benzylcarbamoyl)-4-(4-trifluoromethyl-benzenesulfonyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-5'-carboxylic acid methyl ester

HRID 908587Notes

Reaction equation

Cl.[CH:2]([C:5]1[CH:33]=[CH:32][C:8]([CH2:9][NH:10][C:11]([C@H:13]2[CH2:18][NH:17][CH2:16][CH2:15][N:14]2[S:19]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[O:12])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[CH3:34][O:35][C:36]([C:38]1[CH:43]=[N:42][C:41](Cl)=[CH:40][N:39]=1)=[O:37].C(N(CC)CC)C>CN(C)C=O>[CH3:34][O:35][C:36]([C:38]1[N:39]=[CH:40][C:41]([N:17]2[CH2:16][CH2:15][N:14]([S:19]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:29])[F:30])=[CH:24][CH:23]=3)(=[O:21])=[O:20])[C@@H:13]([C:11](=[O:12])[NH:10][CH2:9][C:8]3[CH:7]=[CH:6][C:5]([CH:2]([CH3:4])[CH3:3])=[CH:33][CH:32]=3)[CH2:18]2)=[N:42][CH:43]=1)=[O:37]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of the compound (61 mg) obtained in Example 1, 5-chloropyrazine-2-carboxylic acid methyl ester (25 mg) and triethylamine (42 μl) in N,N-dimethylformamide (0.3 ml) was stirred at 60° C. for 14 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by thin layer chromatography (5% methanol/chloroform) to give the title compound (75 mg).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe residue was purified by thin layer chromatography (5% methanol/chloroform)

Sources & evidence

ORD record: ord-8db3e873cc0e4100813b0ef05748fe2e
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017612B2

Reaction notes

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