1,3-Cyclopentanedione → HCID 10275049, compound

HRID 1862407Notes

Reaction equation

[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[NH:5][C:4](=[O:13])[CH:3]=1.[Br:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[F:23])[CH:18]=O.[C:24]1(=O)[CH2:28][CH2:27][C:26](=[O:29])[CH2:25]1>C(O)C>[Br:14][C:15]1[CH:16]=[C:17]([CH:18]2[C:3]3[C:4](=[O:13])[NH:5][N:6]([C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=4)[C:2]=3[NH:1][C:24]3[CH2:28][CH2:27][C:26](=[O:29])[C:25]2=3)[CH:20]=[CH:21][C:22]=1[F:23]

Participants

Conditions

Temperature: 80 °C

Procedure

5-Amino-1-(2-pyridyl)-1,2-dihydropyrazol-3-one (0.26 g, 1.5 mmol), prepared as described in (Weisberger A., Porter H. D., J. Am. Chem. Soc., (1944) 66, 1849), 3bromo-4-fluorobenzaldehyde (0.3 g, 1.5 mmol), and 1,3-cyclopentanedione (0.147 g, 1.5 mmol) in ethyl alcohol (3 mL) were heated at 80° C. for 2 days in a sealed tube. The reaction mixture was cooled and the resulting precipitate was filtered off to provide 0.2 g of the title compound as a tan solid. 1H NMR (300 MHz, DMSO-d6) δ 2.32 (m, 2H), 2.8 (m, 2H), 4.82 (s, 1H), 7.22 (m, 3H), 7.48 (dd, 1H), 7.55 (dd, 1H), 7.92 (t, 1H), 8.41 (m, 1H), 10.42 (s, 1H), 10.55 (bs, 1H); MS (ESI−) m/z 439 (M−H)−; Anal. calcd for C2H14N4BrFO2.0.25H2O: C, 53.89;H, 3.28; N, 12.57. Found: C, 53.76;H, 3.01; N, 13.22.

Workup

temperatureThe reaction mixture was cooled
filtrationthe resulting precipitate was filtered off

Sources & evidence

ORD record: ord-1727f5891add4bfa81f4c16f808cdc4e
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06538004B2

Reaction notes

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