2,2-Dimethylpropanethioamide → N-{3-[5-(2-Chloro-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]phenyl}-2,6-difluorobenzenesulfonamide

HRID 1670906Notes

Reaction equation

HRID 1670906 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[S:12][C:11](N3CCCC3)=[N:10][C:9]=2[C:18]2[CH:19]=[C:20]([NH:24][S:25]([C:28]3[C:33]([F:34])=[CH:32][CH:31]=[CH:30][C:29]=3[F:35])(=[O:27])=[O:26])[CH:21]=[CH:22][CH:23]=2)[CH:5]=[CH:4][N:3]=1.ClC1N=C(/C=[C:44](/[C:46]2[CH:47]=C(NS(C3C(F)=CC=CC=3F)(=O)=O)C=C[CH:51]=2)\O)C=CN=1.CC(C)(C)C(=S)N>>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[S:12][C:11]([C:46]([CH3:47])([CH3:51])[CH3:44])=[N:10][C:9]=2[C:18]2[CH:19]=[C:20]([NH:24][S:25]([C:28]3[C:29]([F:35])=[CH:30][CH:31]=[CH:32][C:33]=3[F:34])(=[O:26])=[O:27])[CH:21]=[CH:22][CH:23]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 30311302,2-DimethylpropanethioamideHCID 57989807N-{3-[5-(2-Chloro-4-pyrimidinyl)-2-(1-pyrrolidinyl)-1,3-thiazol-4-yl]phenyl}-2,6-difluorobenzenesulfonamideHCID 136176025N-{3-[(Z)-2-(2-Chloro-4-pyrimidinyl)-1-hydroxyethenyl]phenyl}-2,6-difluorobenzenesulfonamide

Product 1

HCID 57990036N-{3-[5-(2-Chloro-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]phenyl}-2,6-difluorobenzenesulfonamideYield 53.3%

Procedure

Following a procedure analogous to the procedure described in Intermediate 6, using N-{3-[(Z)-2-(2-chloro-4-pyrimidinyl)-1-hydroxyethenyl]phenyl}-2,6-difluorobenzenesulfonamide (1.00 g, 2.36 mmol) and 2,2-dimethylpropanethioamide (0.277 g, 2.36 mmol) the title compound was obtained (690 mg, 53.3% yield). MS (ESI): 521.1 [M+H]+.

Sources & evidence

ORD record
ord-055f2a00552247839e388daa822ddc0e
Source dataset
uspto-grants-2011_08
Patent number
US07994185B2

Reaction notes

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