4-Fluorobenzenesulfonyl chloride → 4-Fluoro-N-((S)-1-{2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-thiazol-4-yl}-3-methyl-butyl)-benzene sulfonamide

HRID 604902Notes

Reaction equation

HRID 604902 reaction equation
Cl.Cl.Cl.[NH2:4][C@H:5]([C:10]1[N:11]=[C:12]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH:26]=[C:25]([CH3:27])[N:24]=[CH:23]3)=[C:18]([O:28][CH3:29])[CH:17]=2)[S:13][CH:14]=1)[CH2:6][CH:7]([CH3:9])[CH3:8].[F:30][C:31]1[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=1>>[F:30][C:31]1[CH:36]=[CH:35][C:34]([S:37]([NH:4][C@H:5]([C:10]2[N:11]=[C:12]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH:26]=[C:25]([CH3:27])[N:24]=[CH:23]4)=[C:18]([O:28][CH3:29])[CH:17]=3)[S:13][CH:14]=2)[CH2:6][CH:7]([CH3:8])[CH3:9])(=[O:39])=[O:38])=[CH:33][CH:32]=1

Participants

3

Reactant 2

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 86624689[4-((S)-1-amino-3-methyl-butyl)-thiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine trihydrochloride

Product 1

HCID 866246974-Fluoro-N-((S)-1-{2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-thiazol-4-yl}-3-methyl-butyl)-benzene sulfonamide

Procedure

The title compound was prepared in analogy to example 36 from 96 mg (0.2 mmol) [4-((S)-1-amino-3-methyl-butyl)-thiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine trihydrochloride and 40 mg (0.2 mmol) 4-fluorobenzenesulfonylchloride. The crude product was purified on silica gel with methylene chloride/methanol 19/1 yielding 85 mg (80%) 4-fluoro-N—((S)-1-{2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-thiazol-4-yl}-3-methyl-butyl)-benzenesulfonamide as a light yellow solid. MS ISP (m/e): 530.0 (100) (M+H)+. 1H NMR (DMSO-D6, 250 MHz): δ (ppm)=10.24 (s, 1H), 8.16 (d, 1H), 7.78-7.65 (m, 3H), 7.23-7.17 (m, 3H), 7.03 (s, 1H), 7.02 (d, 1H), 4.23 (q, 1H), 3.83 (s, 3H), 2.15 (s, 3H), 1.59 (m, 2H), 1.49 (m, 1H), 0.82 (d, 3H), 0.76 (d, 3H).

Workup

  1. customThe crude product was purified on silica gel with methylene chloride/methanol 19/1 yielding 85 mg (80%) 4-fluoro-N—((S)-1-{2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-thiazol-4-yl}-3-methyl-butyl)-benzenesulfonamide as a light yellow solid

Sources & evidence

ORD record
ord-7e7a542e4ff647dfae9ec42de6f90f70
Source dataset
uspto-grants-2011_03
Patent number
US07910740B2

Reaction notes

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