3-Fluorobenzenesulfonyl Chloride → N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]-2,4-difluorophenyl}-3-fluorobenzenesulfonamide

HRID 1671154Notes

Reaction equation

HRID 1671154 reaction equation
ClC1N=C(C2SC(C(C)C)=NC=2C2C=C(NS(C3C(F)=CC=CC=3F)(=O)=O)C=CC=2)C=CN=1.[Cl:34][C:35]1[N:40]=[C:39]([C:41]2[S:45][C:44]([C:46]([CH3:49])([CH3:48])[CH3:47])=[N:43][C:42]=2[C:50]2[C:51]([F:58])=[C:52]([NH2:57])[CH:53]=[CH:54][C:55]=2[F:56])[CH:38]=[CH:37][N:36]=1.[F:59][C:60]1[CH:61]=[C:62]([S:66](Cl)(=[O:68])=[O:67])[CH:63]=[CH:64][CH:65]=1>>[Cl:34][C:35]1[N:40]=[C:39]([C:41]2[S:45][C:44]([C:46]([CH3:49])([CH3:48])[CH3:47])=[N:43][C:42]=2[C:50]2[C:51]([F:58])=[C:52]([NH:57][S:66]([C:62]3[CH:63]=[CH:64][CH:65]=[C:60]([F:59])[CH:61]=3)(=[O:68])=[O:67])[CH:53]=[CH:54][C:55]=2[F:56])[CH:38]=[CH:37][N:36]=1

Participants

4

Reactant 3

HCID 27342583-Fluorobenzenesulfonyl ChlorideHCID 57989911{3-[5-(2-Chloro-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]-2,4-difluorophenyl}amineHCID 57990030N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(1-methylethyl)-1,3-thiazol-4-yl]phenyl}-2,6-difluorobenzenesulfonamide

Product 1

HCID 57989835N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]-2,4-difluorophenyl}-3-fluorobenzenesulfonamide

Procedure

Following a procedure analogous to the procedure described in Intermediate 14 using {3-[5-(2-chloro-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]-2,4-difluorophenyl}amine (500 mg, 1.313 mmol) and 3-fluorobenzenesulfonyl chloride (0.210 mL, 1.575 mmol), the title compound was obtained as an yellow foam (690 mg, 98% yield).

Sources & evidence

ORD record
ord-bfe308c39def47f2a3d2d438d9a817b7
Source dataset
uspto-grants-2011_08
Patent number
US07994185B2

Reaction notes

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