2,6-Difluorobenzenesulfonyl chloride → N-{3-[5-(2-Chloropyrimidin-4-yl)-2-(morpholin-4-yl)-1,3-thiazol-4-yl]-2-methoxyphenyl}-2,6-difluorobenzene-1-sulfonamide

HRID 1671026

Reaction equation

HRID 1671026 reaction equation
ClC1N=C(C2SC(C(C)C)=NC=2C2C=C(N[S:23]([C:26]3[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:27]=3[F:33])(=[O:25])=[O:24])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]([O:59][CH3:60])=[C:54]([CH:56]=[CH:57][CH:58]=2)[NH2:55])[CH:38]=[CH:37][N:36]=1.FC1C=CC=C(F)C=1S(Cl)(=O)=O>>[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]([O:59][CH3:60])=[C:54]([NH:55][S:23]([C:26]3[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:27]=3[F:33])(=[O:25])=[O:24])[CH:56]=[CH:57][CH:58]=2)[CH:38]=[CH:37][N:36]=1

Participants

4

Reactant 3

HCID 27342712,6-Difluorobenzenesulfonyl chlorideHCID 579897953-(5-(2-Chloropyrimidin-4-yl)-2-morpholinothiazol-4-yl)-2-methoxyanilineHCID 57990030N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(1-methylethyl)-1,3-thiazol-4-yl]phenyl}-2,6-difluorobenzenesulfonamide

Product 1

HCID 53487989N-{3-[5-(2-Chloropyrimidin-4-yl)-2-(morpholin-4-yl)-1,3-thiazol-4-yl]-2-methoxyphenyl}-2,6-difluorobenzene-1-sulfonamideYield 27.2%

Procedure

Following a procedure analogous to the procedure described in Intermediate 14 using 3-(5-(2-chloropyrimidin-4-yl)-2-morpholinothiazol-4-yl)-2-methoxyaniline (26.1 g, 64.7 mmol) and 2,6-difluorobenzene-1-sulfonyl chloride (13.8 g, 64.7 mmol) the title compound of Step C was obtained (10.2 g, 27.2% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.23 (d, J=5.5 Hz, 1H), 7.62-7.71 (m, 1H), 7.38-7.45 (m, 1H), 7.15-7.30 (m, 4H), 6.40 (d, J=5.5 Hz, 1H), 3.67-3.78 (m, 4H), 3.50-3.61 (m, 4H), 3.18 (s, 3H). MS (ES+): 580 [M+H]+.

Sources & evidence

ORD record
ord-9f34fd5bd8c44900b4e7ac94ae24cb4d
Source dataset
uspto-grants-2011_08
Patent number
US07994185B2

Linked notes

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