m-Chloroperbenzoic acid → 3-(benzyloxy)-N-(4-methylthiazol-2-yl)-5-(phenylsulfinyl)pyridin-2-amine hydrochloride

HRID 1426121Notes

Reaction equation

HRID 1426121 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([NH:22][C:23]2[S:24][CH:25]=[C:26]([CH3:28])[N:27]=2)=[N:11][CH:12]=[C:13]([S:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=C([Cl:35])C=C(C(OO)=[O:37])C=1>>[ClH:35].[CH2:1]([O:8][C:9]1[C:10]([NH:22][C:23]2[S:24][CH:25]=[C:26]([CH3:28])[N:27]=2)=[N:11][CH:12]=[C:13]([S:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:37])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 59225645HCID 59225645, compound

Product 1

HCID 866396713-(benzyloxy)-N-(4-methylthiazol-2-yl)-5-(phenylsulfinyl)pyridin-2-amine hydrochlorideYield 50.6%

Procedure

3-(Benzyloxy)-N-(4-methylthiazol-2-yl)-5-(phenylthio)pyridin-2-amine (0.049 g, 0.121 mmol) (prepared according to Example 7; 0.049 g, 0.121 mmol) and MCPBA (0.0398 g, 0.166 mmol) were reacted according to Example 8 to provide 3-(benzyloxy)-N-(4-methylthiazol-2-yl)-5-(phenylsulfinyl)pyridin-2-amine hydrochloride (0.028 g, 50.6% yield). 1H NMR (DMSO-d6) δ 8.25 (d, 1H), 7.70 (m, 2H), 7.59 (s, 1H), 7.56 (m, 5H), 7.34 (m, 3H), 6.79 (s, 1H), 5.31 (s, 2H), 2.28 (s, 3H). Mass spectrum (apci) m/z=422.0 (M+H-HCl).

Sources & evidence

ORD record
ord-cf22a38222134b53aff5f0b8e1364189
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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