1,3-Cyclopentanedione → HCID 10199630, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=O.[CH2:11]1[C:16](=O)[CH2:15][C:13](=[O:14])[CH2:12]1.[NH2:18][C:19]1[NH:23][N:22]([CH3:24])[C:21](=[O:25])[CH:20]=1>>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]2[C:20]3[C:21](=[O:25])[N:22]([CH3:24])[NH:23][C:19]=3[NH:18][C:16]3[CH2:11][CH2:12][C:13](=[O:14])[C:15]2=3)[CH:7]=[CH:8][C:9]=1[F:10]Participants
4
Procedure
3-Bromo-4-fluorobenzaldehyde (0.3 g, 1.5 mmol), 1,3-cyclopentadione (0.15 g, 1.5 mmol), and 5-amino-2-methyl-1,2-dihydropyrazol-3-one (0.17 g, 1.5 mmol), prepared by the method of (C. Taylor and J. Barton, J.Am.ChemSoc., (1959) 81, 2448) were processed as described in Example 1 to provide 0.32 g of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 2.21 (t, 2H), 2.59 (m, 2H), 3.38 (s, 3H), 4.75 (s, 1H), 7.13 (m, 1H), 7.2 (t, 1H), 7.42 (dd, 1H), 10.16 (s, 1H), 10.51 (bs, 1H); MS (ESI−) m/z 378 (M−H)−; Anal. Calcd for C16H13N3BrFO2: C, 50.21; H, 3.56; N, 10.98. Found: C, 50.76; H, 4.09; N, 10.52.
Sources & evidence
- ORD record
- ord-3435048e00bb4af5a49318d4f4c53cb9
- Source dataset
- uspto-grants-2004_08
- Patent number
- US06780872B2
Reaction notes
Loading…