Water → HCID 66738396, compound

HRID 1958309Notes

Reaction equation

[CH3:1][C:2]1[N:3]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=2)[C:4](=[O:22])[C:5]([C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][N:13]=2)=[O:9])=[N:6][CH:7]=1.[Br:33]N1C(=O)CCC1=O.O>CN(C=O)C>[Br:33][C:7]1[N:6]=[C:5]([C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][N:13]=2)=[O:9])[C:4](=[O:22])[N:3]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:30])([F:32])[F:31])[CH:24]=2)[C:2]=1[CH3:1]

Participants

Conditions

Temperature: 50 °C

Procedure

5-Methyl-N-{[5-(methylsulfonyl)-pyridin-2-yl]methyl}-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxamide (0.097 g, 0.21 mmol) was dissolved in DMF (2 ml) in a vial. To this mixture was added N-bromosuccinimide (0.055 g, 0.31 mmol), and the vial was sealed and the mixture was heated at 50° C. with stirring for 1 h. The crude mixture was added dropwise to water (40 ml) under magnetic stirring. The precipitate was isolated by filtration to give 0.105 g (92%) of 6-bromo-5-methyl-N-{[5-(methylsulfonyl)pyridin-2-yl]methyl}-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxamide as a solid.

Workup

customthe vial was sealed
customThe precipitate was isolated by filtration

Sources & evidence

ORD record: ord-463aa13d6ec9447f8867b5f6d332e26d
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410114B2

Reaction notes

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