Hydrochloric Acid → 5-(3-chlorobenzylthio)-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](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+].BrC[C:37]1C=C[CH:40]=[C:39]([Cl:43])[CH:38]=1.Cl>>[ClH:43].[Cl:43][C:39]1[CH:40]=[C:24]([CH:25]=[CH:37][CH:38]=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-(bromomethyl)-3-chlorobenzene (0.022 mL, 0.17 mmol) were reacted according to the method of Example 43 to afford 5-(3-chlorobenzylthio)-3-(benzyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochloride (64.2 mg, 77.70% yield) as a white solid after HCl salt formation. 1H NMR (d6-DMSO) δ 10.85 (bs, 1H), 7.80 (d, 1H), 7.60-7.53 (m, 3H), 7.45-7.33 (m, 3H), 7.31-7.25 (m, 3H), 7.12 (m, 1H), 6.78 (s, 1H), 5.29 (s, 2H), 4.19 (s, 2H), 2.29 (d, 3H); Mass spectrum (apci) m/z=238.0 (100), 454.0 (95), 362.9 (80).
Sources & evidence
- ORD record
- ord-446085e346f9412ca4e0c342f9ae5bd0
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08933077B2
Reaction notes
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