Hydrochloric Acid → 3-(benzyloxy)-N-(4-methylthiazol-2-yl)-5-(pyridin-2-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+].Br.BrC[C:38]1[CH:43]=[CH:42]C=C[N:39]=1.[ClH:44]>>[ClH:44].[ClH:44].[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]=[CH:42][CH:43]=[CH:38][N:39]=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 2-(bromomethyl)pyridine hydrobromide (42.6 mg, 0.17 mmol) were reacted according to the method of Example 43 to afford 3-(benzyloxy)-N-(4-methylthiazol-2-yl)-5-(pyridin-2-ylmethylthio)pyridin-2-amine dihydrochloride (51.6 mg, 62.1% yield) as a white solid after HCl salt formation. 1H NMR (d6-DMSO) δ 10.80 (bs, 1H), 8.63 (d, 1H), 8.04 (t, 1H), 7.81 (d, 1H), 7.60-7.53 (m, 4H), 7.49-7.34 (m, 4H), 6.76 (s, 1H), 5.30 (s, 2H), 4.42 (s, 2H), 2.28 (d, 3H); Mass spectrum (apci) m/z=330.0 (100), 421.0 (95), 238.0 (50).
Sources & evidence
- ORD record
- ord-e33d963b28a242ff926b4350f3ab3e17
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08933077B2
Reaction notes
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