Hydrochloric Acid → 5-(4-chlorobenzylthio)-3-(benzyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochloride

HRID 1426125Notes

Reaction equation

HRID 1426125 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:22][CH2:23][CH2:24][C:25](OC)=O)[CH:12]=[N:13][C:14]=1[NH:15][C:16]1[S:17][CH:18]=[C:19]([CH3:21])[N:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC([O-])(C)C.[K+].[Cl:35][C:36]1[CH:41]=CC(CCl)=[CH:38][CH:37]=1.Cl>>[ClH:35].[Cl:35][C:36]1[CH:41]=[CH:25][C:24]([CH2:23][S:22][C:11]2[CH:10]=[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:14]([NH:15][C:16]3[S:17][CH:18]=[C:19]([CH3:21])[N:20]=3)=[N:13][CH:12]=2)=[CH:38][CH:37]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 16660505Methyl 3-(5-(benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-ylthio)propanoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 866396745-(4-chlorobenzylthio)-3-(benzyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochlorideYield 137.2%

Procedure

Methyl 3-(5-(benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-ylthio)propanoate (prepared according to Example 42; 70 mg, 0.17 mmol), KOtBu (0.59 mL, 0.59 mmol) and 1-chloro-4-(chloromethyl)benzene (27 mg, 0.17 mmol) were reacted according to the method of Example 43 to afford 5-(4-chlorobenzylthio)-3-(benzyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochloride (57.2 mg, 69.2% yield) as a white solid after HCl salt formation. 1H NMR (d6-DMSO) δ 10.85 (bs, 1H), 7.79 (d, 1H), 7.57 (m, 2H), 7.53 (d, 1H), 7.45-7.34 (m, 3H), 7.30 (m, 2H), 7.18 (m, 2H), 6.78 (s, 1H), 5.29 (s, 2H), 4.17 (s, 2H), 2.29 (d, 3H); Mass spectrum (apci) m/z=238.0 (100), 454.0 (75), 362.9 (60).

Sources & evidence

ORD record
ord-ef4409145efe44369718af9930424491
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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