4-(4-chloro-2-(2-oxoindolin-5-yl)phenoxy)-N-(2,4-dimethoxybenzyl)-2,5-difluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide → 4-(4-chloro-2-(2-oxoindolin-5-yl)phenoxy)-2,5-difluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide

HRID 2203444Notes

Reaction equation

HRID 2203444 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:32][C:33]2[CH:38]=[C:37]([F:39])[C:36]([S:40](=[O:59])(=[O:58])[N:41](CC3C=CC(OC)=CC=3OC)[C:42]3[S:46][N:45]=[CH:44][N:43]=3)=[CH:35][C:34]=2[F:60])=[C:6]([C:8]2[CH:9]=[CH:10][C:11]3ON=[C:13]([N:16]([C:24](OC(C)(C)C)=[O:25])C(OC(C)(C)C)=O)[C:12]=3[CH:31]=2)[CH:7]=1.ClC1C=CC(OC2C(F)=CC(S(N(CC3C=CC(OC)=CC=3OC)C3SN=CN=3)(=O)=O)=C(F)C=2)=C(C2C=C3C(=CC=2)NC(=O)C3)C=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:32][C:33]2[C:34]([F:60])=[CH:35][C:36]([S:40]([NH:41][C:42]3[S:46][N:45]=[CH:44][N:43]=3)(=[O:59])=[O:58])=[C:37]([F:39])[CH:38]=2)=[C:6]([C:8]2[CH:31]=[C:12]3[C:13](=[CH:10][CH:9]=2)[NH:16][C:24](=[O:25])[CH2:11]3)[CH:7]=1

Participants

3

Reactant 2

HCID 903891774-(4-chloro-2-(2-oxoindolin-5-yl)phenoxy)-N-(2,4-dimethoxybenzyl)-2,5-difluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamideHCID 123740120Di-tert-butyl [5-(5-chloro-2-{4-[(2,4-dimethoxybenzyl)(1,2,4-thiadiazol-5-yl)sulfamoyl]-2,5-difluorophenoxy}phenyl)-1,2-benzoxazol-3-yl]imidodicarbonate

Product 1

HCID 715590704-(4-chloro-2-(2-oxoindolin-5-yl)phenoxy)-2,5-difluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamideYield 53%

Procedure

Following the procedure as described in EXAMPLE 44, making non-critical variations to replace di-tert-butyl [5-(5-chloro-2-{4-[(2,4-dimethoxybenzyl)(1,2,4-thiadiazol-5-yl)sulfamoyl]-2,5-difluorophenoxy}phenyl)-1,2-benzoxazol-3-yl]imidodicarbonate with 4-(4-chloro-2-(2-oxoindolin-5-yl)phenoxy)-N-(2,4-dimethoxybenzyl)-2,5-difluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide, 4-(4-chloro-2-(2-oxoindolin-5-yl)phenoxy)-2,5-difluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide was obtained as an off-white solid in 53% yield over two steps (0.03 g): 1H NMR (300 MHz, DMSO-d6) δ10.48 (s, 1H), 8.52 (s, 1H), 7.74 (dd, J=9.9, J=6.4 Hz, 1H), 7.52 (d, J=2.6 Hz, 1H), 7.43 (dd, J=8.7, 2.6 Hz, 1H), 7.35 (br s, 1H), 7.31 (dd, J=8.1, 1.4 Hz, 1H), 7.23 (d, J=8.7 Hz, 1H), 7.09 (dd, J=10.5, 6.5 Hz, 1H), 6.83 (d, J=8.0 Hz, 1H), 3.47 (s, 2H), (NH not observed); MS (ES+) m/z 534.8 (M+1), 536.8 (M+1).

Sources & evidence

ORD record
ord-fd271a27f0074e478729d994ae2490f0
Source dataset
uspto-grants-2016_06
Patent number
US09365578B2

Reaction notes

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