Methanesulfonyl chloride → HCID 86624699, compound

HRID 604904Notes

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].[CH3:30][S:31](Cl)(=[O:33])=[O:32]>>[CH3:29][O:28][C:18]1[CH:17]=[C:16]([NH:15][C:12]2[S:13][CH:14]=[C:10]([C@@H:5]([NH:4][S:31]([CH3:30])(=[O:33])=[O:32])[CH2:6][CH:7]([CH3:8])[CH3:9])[N:11]=2)[CH:21]=[CH:20][C:19]=1[N:22]1[CH:26]=[C:25]([CH3:27])[N:24]=[CH:23]1

Participants

Reactant 2

HCID 31297Methanesulfonyl chloride

HCID 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 86624699HCID 86624699, compound

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 23 mg (0.2 mmol) methyl sulfonyl chloride. The crude product was purified on silica gel with methylene chloride/methanol 19/1 yielding 45 mg (50%) N—((S)-1-{2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-thiazol-4-yl}-3-methyl-butyl)-methanesulfonamide as a light yellow solid. MS ISP (m/e): 450.1 (100) (M+H)+. 1H NMR (DMSO-D6, 250 MHz): δ (ppm)=10.40 (s, 1H), 7.90 (s, 1H), 7.65 (s, 1H), 7.54 (d, 1H), 7.24 (d, 1H), 7.06 (d, 1H), 7.03 (s, 1H), 6.81 (s, 1H), 4.36 (q, 1H), 3.84 (s, 3H), 2.14 (s, 3H), 1.65 (m, 3H), 0.89 (m, 6H).

Workup

customThe crude product was purified on silica gel with methylene chloride/methanol 19/1 yielding 45 mg (50%) N—((S)-1-{2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-thiazol-4-yl}-3-methyl-butyl)-methanesulfonamide as a light yellow solid

Sources & evidence

ORD record: ord-d83c97afe6844eadb6086a5a6adb580d
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910740B2

Reaction notes

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