Hydrochloric Acid → 3-(benzyloxy)-N-(4-methylthiazol-2-yl)-5-(pyridin-3-ylmethylthio)pyridin-2-amine dihydrochloride
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+].[ClH:35].[Cl:36][CH2:37][C:38]1[CH:39]=[N:40]C=CC=1.Cl>>[ClH:36].[ClH:35].[CH2:1]([O:8][C:9]1[C:14]([NH:15][C:16]2[S:17][CH:18]=[C:19]([CH3:21])[N:20]=2)=[N:13][CH:12]=[C:11]([S:22][CH2:23][C:24]2[CH:25]=[N:40][CH:39]=[CH:38][CH:37]=2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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 3-(chloromethyl)pyridine hydrochloride (27.6 mg, 0.17 mmol were reacted according to the method of Example 43 to afford 3-(benzyloxy)-N-(4-methylthiazol-2-yl)-5-(pyridin-3-ylmethylthio)pyridin-2-amine dihydrochloride (44.2 mg, 53.2% yield) as a white solid after HCl salt formation. 1H NMR (d6-DMSO) δ 8.68 (dd, 1H), 8.65 (d, 1H), 8.11 (m, 1H), 7.80-7.75 (m, 2H), 7.60-7.55 (m, 3H), 7.45-7.34 (m, 3H), 6.75 (s, 1H), 5.30 (s, 2H), 4.34 (s, 2H), 2.28 (d, 3H); Mass spectrum (apci) m/z=238.0 (100), 330.0 (70), 421.0 (60).
Sources & evidence
- ORD record
- ord-1a5a9ef0f2504ac9ab2a51aa9b492671
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08933077B2
Reaction notes
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