2-Pyridone → HCID 57744440, compound
Reaction equation
[NH:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]1=[O:7].Br[C:9]1[S:10][C:11]([C:15]([NH:17][CH2:18][C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[O:16])=[C:12]([CH3:14])[N:13]=1>>[CH3:14][C:12]1[N:13]=[C:9]([N:1]2[CH:6]=[CH:5][CH:4]=[CH:3][C:2]2=[O:7])[S:10][C:11]=1[C:15]([NH:17][CH2:18][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)=[O:16]Participants
3
Procedure
Following the procedure as described in Example 3, making variations only as required to use pyridin-2(1H)-one in place of 4-aminopyridin-2(1H)-one to react with 2-bromo-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide, the title compound was obtained as a colorless solid in 21% yield: mp 218-220° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, DMSO-d6) δ 8.87 (t, J=5.6 Hz, 1H), 8.71 (dd, J=7.3, 1.3 Hz, 1H), 8.56-8.43 (m, 2H), 7.71 (d, J=7.3 Hz, 1H), 7.68-7.59 (m, 1H), 7.38 (br s, 1H), 6.74 (d, J=9.2 Hz, 1H), 6.60-6.55 (m, 1H), 4.42 (d, J=5.7 Hz, 2H), 2.56 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 161.9, 160.2, 153.8, 150.8, 149.3, 148.4, 141.4, 135.5, 131.5, 124.2, 120.9, 108.7, 41.0, 17.5; MS (ES+) m/z 327.2 (M+1).
Sources & evidence
- ORD record
- ord-a8375f76fa7d4b43a56bc90a77d66340
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08501746B2
Reaction notes
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