Methanesulfonyl chloride → (5-Methanesulfonyl-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-yl)-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine

HRID 604910Notes

Reaction equation

Cl.Cl.Cl.[CH3:4][O:5][C:6]1[CH:7]=[C:8]([NH:18][C:19]2[S:20][C:21]3[CH2:22][NH:23][CH2:24][CH2:25][C:26]=3[N:27]=2)[CH:9]=[CH:10][C:11]=1[N:12]1[CH:16]=[C:15]([CH3:17])[N:14]=[CH:13]1.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>>[CH3:28][S:29]([N:23]1[CH2:24][CH2:25][C:26]2[N:27]=[C:19]([NH:18][C:8]3[CH:9]=[CH:10][C:11]([N:12]4[CH:16]=[C:15]([CH3:17])[N:14]=[CH:13]4)=[C:6]([O:5][CH3:4])[CH:7]=3)[S:20][C:21]=2[CH2:22]1)(=[O:31])=[O:30]

Participants

Reactant 2

HCID 31297Methanesulfonyl chloride

HCID 25106280N-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-amine trihydrochloride

Product 1

HCID 25106368(5-Methanesulfonyl-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-yl)-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine

Procedure

The title compound was prepared in analogy to example 45 from 90 mg (0.2 mmol) [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-(4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-yl)-amine trihydrochloride and 23 mg (0.2 mmol) methanesulfonyl chloride yielding 39 mg (46%) (5-methanesulfonyl-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-yl)-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine as a yellow solid. MS ISP (m/e): 420.1 (100) (M+H)+. 1H NMR (DMSO-D6, 250 MHz): δ (ppm)=10.38 (s, 1H), 7.65 (s, 1H), 7.48 (s, 1H), 7.30 (d, 1H), 7.25 (d, 1H), 7.02 (s, 1H), 4.34 (br s, 2H), 3.79 (s, 3H), 3.52 (t, 2H), 2.96 (s, 3H), 2.76 (br t, 2H), 2.14 (s, 3H).

Sources & evidence

ORD record: ord-73805f79a1ce4f7ab3a92955a7a43c8b
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910740B2

Reaction notes

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