2-Chloro-4-methylpyrimidine → N-{2-chloro-3-[(E)-2-(2-chloro-4-pyrimidinyl)-1-hydroxyethenyl]phenyl}-2,6-difluorobenzenesulfonamide

HRID 590059

Reaction equation

HRID 590059 reaction equation
[Cl:1][C:2]1[C:11]([NH:12][S:13]([C:16]2[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:17]=2[F:23])(=[O:15])=[O:14])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=O.[Cl:24][C:25]1[N:30]=[C:29]([CH3:31])[CH:28]=[CH:27][N:26]=1>>[Cl:1][C:2]1[C:3](/[C:4](/[OH:6])=[CH:31]\[C:29]2[CH:28]=[CH:27][N:26]=[C:25]([Cl:24])[N:30]=2)=[CH:8][CH:9]=[CH:10][C:11]=1[NH:12][S:13]([C:16]1[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:17]=1[F:23])(=[O:15])=[O:14]

Participants

3

Reactant 2

HCID 116296072-Chloro-4-methylpyrimidineHCID 57989637Methyl 2-chloro-3-(2,6-difluorophenylsulfonamido)benzoate

Product 1

HCID 136342910N-{2-chloro-3-[(E)-2-(2-chloro-4-pyrimidinyl)-1-hydroxyethenyl]phenyl}-2,6-difluorobenzenesulfonamideYield 73.5%

Procedure

Following a procedure analogous to Intermediate 5, Step B using methyl 2-chloro-3-(2,6-difluorophenylsulfonamido)benzoate (31 g, 85.9 mmol) and 2-chloro-4-methylpyrimidine (12.2 g, 94.5 mmol) the title compound was obtained (33 g, 73.5% yield). 1H NMR (400 MHz, CDCl3) δ ppm 13.47-13.52 (br, 0.96H), 8.50-8.56 (m, 0.13H), 8.38 (d, J=5.3 Hz, 1H), 7.78-7.82 (m, 0.15H), 7.62-7.73 (m, 2H), 7.40-7.50 (m, 1.18H), 7.17-7.30 (m, 1.77H), 6.90-6.97 (m, 2.29H), 6.83 (d, J=5.3 Hz, 1H), 5.65 (s, 1H), 4.28 (s, 0.26H). MS (ES+): 458 [M+H]+.

Sources & evidence

ORD record
ord-f579e594208b44978abbe87a969c3aa7
Source dataset
uspto-grants-2016_01
Patent number
US09233956B2

Linked notes

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