Ethanolamine → 5-(5-Ethyl-2-methyl-6-oxo-1,6-dihydropyridin-3-yl)thiophene-2-sulfonic acid (2-hydroxyethyl)amide
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].[NH2:20][CH2:21][CH2:22][OH:23]>>[OH:23][CH2:22][CH2:21][NH:20][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-aminoethanol as described in Step 5, Example 24 to give the title compound as a yellow solid (38% yield). LC/MS: RT 2.20 min; m/e 343 (M+H); 1H NMR (δ, ppm): 11.80 (1H, br), 7.80 (1H, s), 7.53 (1H, d), 7.32 (1H, s), 7.13 (1H, d), 4.72 (1H, t), 3.26-3.42 (2H, m), 2.90 (2H, t), 2.30-2.60 (3H, s), 2.4 (2H, q), 1.10 (3H, t).
Sources & evidence
- ORD record
- ord-5353a81e988d4a5990f2a1bf3d45d918
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08173682B2
Reaction notes
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