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

HRID 1670908Notes

Reaction equation

HRID 1670908 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](/[CH:8]=[C:9](/[C:11]2[CH:12]=[C:13]([NH:17][S:18]([C:21]3[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=3F)(=[O:20])=[O:19])[CH:14]=[CH:15][CH:16]=2)\[OH:10])[CH:5]=[CH:4][N:3]=1.[F:29]C1C=CC(F)=CC=1S(NC1C=C(C=CC=1)C(OC)=O)(=O)=O.ClC1N=C(C)C=CN=1>>[Cl:1][C:2]1[N:7]=[C:6](/[CH:8]=[C:9](/[C:11]2[CH:12]=[C:13]([NH:17][S:18]([C:21]3[CH:22]=[C:23]([F:29])[CH:24]=[CH:25][C:26]=3[F:27])(=[O:19])=[O:20])[CH:14]=[CH:15][CH:16]=2)\[OH:10])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 116296072-Chloro-4-methylpyrimidineHCID 16344470Methyl 3-{[(2,5-difluorophenyl)sulfonyl]amino}benzoateHCID 136176025N-{3-[(Z)-2-(2-Chloro-4-pyrimidinyl)-1-hydroxyethenyl]phenyl}-2,6-difluorobenzenesulfonamide

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-21231deae3ad4975ac1c5804a8e4afa5
Source dataset
uspto-grants-2011_08
Patent number
US07994185B2

Reaction notes

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