N-Methylphenylethanolamine → 5-(5-Ethyl-2-methyl-6-oxo-1,6-dihydropyridin-3-yl)thiophene-2-sulfonic acid (2-hydroxy-2-phenylethyl)methylamide
Reaction equation
[CH2:1]([C:3]1[C:8](=[O:9])[NH:7][C:6]([CH3:10])=[C:5]([C:11]2[S:15][C:14]([S:16](Cl)(=[O:18])=[O:17])=[CH:13][CH:12]=2)[CH:4]=1)[CH3:2].[OH:20][CH:21]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:22][NH:23][CH3:24]>>[OH:20][CH:21]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:22][N:23]([CH3:24])[S:16]([C:14]1[S:15][C:11]([C:5]2[CH:4]=[C:3]([CH2:1][CH3:2])[C:8](=[O:9])[NH:7][C:6]=2[CH3:10])=[CH:12][CH:13]=1)(=[O:18])=[O:17]Participants
3
Procedure
5-(5-Ethyl-2-methyl-6-oxo-1,6-dihydropyridin-3-yl)thiophene-2-sulfonyl chloride is reacted with (2-hydroxy-2-phenylethyl)methylamine as described in Step 5, Example 24 to give the title compound as a solid (58% yield). LC/MS: RT 2.93 min; m/e 433 (M+H); 1H NMR (δ, ppm): 11.81 (1H, s), 7.59 (1H, d), 7.34 (6H, m); 7.19 (1H, d), 5.61 (1H, d), 4.78 (1H, q), 3.12 (2H), 2.78 (3H, s), 2.38 (2H), 2.31 (3H, s), 1.09 (3H, t).
Sources & evidence
- ORD record
- ord-2246c1de6d324dfca14ebbd0542ac4bb
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08173682B2
Reaction notes
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