5-amino-1-methyl-2,3-dihydro-1H-pyrazol-3-one → HCID 10181781, compound
Reaction equation
[O:1]1[CH2:6][C:5](=O)[CH2:4][C:3](=[O:8])[CH2:2]1.[I:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[F:18])[CH:13]=O.[NH2:19][C:20]1[N:24]([CH3:25])[NH:23][C:22](=[O:26])[CH:21]=1>>[F:18][C:17]1[CH:16]=[CH:15][C:12]([CH:13]2[C:21]3[C:22](=[O:26])[NH:23][N:24]([CH3:25])[C:20]=3[NH:19][C:5]3[CH2:6][O:1][CH2:2][C:3](=[O:8])[C:4]2=3)=[CH:11][C:10]=1[I:9]Participants
4
Procedure
2H-Pyran-3,5(4H,6H)-dione (0.085 g, 0.75 mmol), 3-iodo-4-fluoro-benzaldehyde (0.182 g, 0.75 mmol) and 5-amino-1-methyl-1,2-dihydropyrazol-3-one (0.084 g, 0.75 mmol) were processed as described in Example 26C to provide 0.23 g of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 3.5 (s, 3H), 4.0 (s, 2H), 4.52 (q, 2H), 4.92 (s, 1H), 7.1 (t, 1H), 7.18 (m, 1H), 7.55 (dd, 1H), 9.62 (bs, 1H), 10.1 (s, 1H); MS (ESI−) m/z 440 (M−H)−; Anal. calcd for C16H13N3FIO3.C2H5OH: C, 44.37; H, 3.93; N, 8.62. Found: C, 44.38; H, 3.89; N, 8.74.
Sources & evidence
- ORD record
- ord-7a15ecb6842245e087bd54462e999bc9
- Source dataset
- uspto-grants-2004_08
- Patent number
- US06780872B2
Reaction notes
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