2-Chloro-4-methylpyrimidine → N-{3-[(Z)-2-(2-Chloro-4-pyrimidinyl)-1-hydroxyethenyl]phenyl}-2,5-difluorobenzenesulfonamide

HRID 590015Notes

Reaction equation

HRID 590015 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=1)[C:16]([O:18]C)=O)(=[O:11])=[O:10].[Cl:23][C:24]1[N:29]=[C:28]([CH3:30])[CH:27]=[CH:26][N:25]=1>>[Cl:23][C:24]1[N:29]=[C:28](/[CH:30]=[C:16](/[C:15]2[CH:14]=[C:13]([NH:12][S:9]([C:3]3[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=3[F:1])(=[O:10])=[O:11])[CH:22]=[CH:21][CH:20]=2)\[OH:18])[CH:27]=[CH:26][N:25]=1

Participants

3

Reactant 2

HCID 116296072-Chloro-4-methylpyrimidineHCID 16344470Methyl 3-{[(2,5-difluorophenyl)sulfonyl]amino}benzoate

Product 1

HCID 136088569N-{3-[(Z)-2-(2-Chloro-4-pyrimidinyl)-1-hydroxyethenyl]phenyl}-2,5-difluorobenzenesulfonamideYield 85.3%

Procedure

Following a procedure analogous to the procedure described in Intermediate 5, Step B using methyl 3-(2,5-difluorophenylsulfonamido)benzoate (20.5 g, 62.7 mmol) and 2-chloro-4-methylpyrimidine (8.8 g, 68.9 mmol) the title compound was obtained (22.6 g, 85.3% yield). 1H NMR (400 MHz, CDCl3) δ ppm 13.40-13.50 (br s), 10.95-11.12 (br s), 8.72-8.80 (m), 8.57-8.63 (m), 7.77-7.82 (m), 7.36-7.72 (m), 7.22-7.30 (m), 6.43 (s), 4.52 (s); m/z (ES+): 424 [M+H]+.

Sources & evidence

ORD record
ord-c634fb4021d04f61bb3325abb28f79e7
Source dataset
uspto-grants-2016_01
Patent number
US09233956B2

Reaction notes

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