Hydrochloric Acid → 5-(2-methoxybenzylthio)-3-(benzyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochloride
Reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:22][CH2:23][CH2:24][C:25]([O:27][CH3:28])=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][CH2:36][C:37]1C=CC=[CH:39][C:38]=1OC.Cl>>[ClH:35].[CH3:28][O:27][C:25]1[CH:39]=[CH:38][CH:37]=[CH:36][C:24]=1[CH2:23][S:22][C:11]1[CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:14]([NH:15][C:16]2[S:17][CH:18]=[C:19]([CH3:21])[N:20]=2)=[N:13][CH:12]=1Participants
5
Reactant 4
Product 1
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-(chloromethyl)-2-methoxybenzene (0.023 mL, 0.17 mmol) were reacted according to the method of Example 43 to afford 5-(2-methoxybenzylthio)-3-(benzyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochloride (63.3 mg, 77.3% yield) as a white solid after HCl salt formation. 1H NMR (d6-DMSO) δ 7.79 (d, 1H), 7.57 (m, 2H), 7.49 (d, 1H), 7.45-7.33 (m, 3H), 7.23 (m, 1H), 6.98 (m, 2H), 6.79 (m, 2H), 5.28 (s, 2H), 4.09 (s, 2H), 3.74 (s, 3H), 2.29 (s, 3H); Mass spectrum (apci) m/z=450.0 (100), 359.0 (45), 238.0 (40).
Sources & evidence
- ORD record
- ord-89eb7bffdca1455b8857b14591e34186
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08933077B2
Reaction notes
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