2,5-Difluorobenzenesulfonyl chloride → N-{3-[5-(2-Chloro-4-pyrimidinyl)-2-(4-morpholinyl)-1,3-thiazol-4-yl]-2,4-difluorophenyl}-2,5-difluorobenzenesulfonamide

HRID 1671125Notes

Reaction equation

HRID 1671125 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]([N:46]3[CH2:51][CH2:50][O:49][CH2:48][CH2:47]3)=[N:43][C:42]=2[C:52]2[C:53]([F:60])=[C:54]([CH:56]=[CH:57][C:58]=2[F:59])[NH2:55])[CH:38]=[CH:37][N:36]=1.[F:61][C:62]1[CH:67]=[CH:66][C:65]([F:68])=[CH:64][C:63]=1[S:69](Cl)(=[O:71])=[O:70]>>[Cl:34][C:35]1[N:40]=[C:39]([C:41]2[S:45][C:44]([N:46]3[CH2:47][CH2:48][O:49][CH2:50][CH2:51]3)=[N:43][C:42]=2[C:52]2[C:53]([F:60])=[C:54]([NH:55][S:69]([C:63]3[CH:64]=[C:65]([F:68])[CH:66]=[CH:67][C:62]=3[F:61])(=[O:71])=[O:70])[CH:56]=[CH:57][C:58]=2[F:59])[CH:38]=[CH:37][N:36]=1

Participants

4

Reactant 3

HCID 27369112,5-Difluorobenzenesulfonyl chlorideHCID 57989700HCID 57989700, compoundHCID 57990030N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(1-methylethyl)-1,3-thiazol-4-yl]phenyl}-2,6-difluorobenzenesulfonamide

Product 1

HCID 57989715N-{3-[5-(2-Chloro-4-pyrimidinyl)-2-(4-morpholinyl)-1,3-thiazol-4-yl]-2,4-difluorophenyl}-2,5-difluorobenzenesulfonamide

Procedure

Following a procedure analogous to the procedure described in Intermediate 14 using 3-[5-(2-chloro-4-pyrimidinyl)-2-(4-morpholinyl)-1,3-thiazol-4-yl]-2,4-difluoroaniline (900 mg, 2.196 mmol) and 2,5-difluorobenzenesulfonyl chloride (0.355 mL, 2.64 mmol) the title compound of Step H was obtained as a light yellow solid (774 mg, 60% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.41 (d, J=5.5 Hz, 1H), 7.48-7.57 (m, 4H), 7.29 (t, J=8.8 Hz, 1H), 6.57 (d, J=5.5 Hz, 1H), 3.70-3.74 (m, 4H), 3.52-3.55 (m, 4H). MS (ESI): 585 [M+H]+.

Sources & evidence

ORD record
ord-d239d4d20006481cbe6bd1de5197146a
Source dataset
uspto-grants-2011_08
Patent number
US07994185B2

Reaction notes

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