Ethyl cyanoacetate → HCID 10157303, compound

HRID 1837049Notes

Reaction equation

HRID 1837049 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][CH3:8])[NH:5][C:4](=[O:9])[CH:3]=1.C(NN)C.C(CC(OCC)=O)#N.[Br:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][C:30]=1[F:31])[CH:26]=O.[C:32]1(=O)[CH2:36][CH2:35][C:34](=[O:37])[CH2:33]1>C(O)C>[Br:22][C:23]1[CH:24]=[C:25]([CH:26]2[C:3]3[C:4](=[O:9])[NH:5][N:6]([CH2:7][CH3:8])[C:2]=3[NH:1][C:32]3[CH2:36][CH2:35][C:34](=[O:37])[C:33]2=3)[CH:28]=[CH:29][C:30]=1[F:31]

Participants

7

Reactant 5

HCID 7764Ethyl cyanoacetateHCID 29062EthylhydrazineHCID 774661,3-CyclopentanedioneHCID 1736043-Bromo-4-fluorobenzaldehydeHCID 23261257HCID 23261257, compound

Product 1

HCID 10157303HCID 10157303, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Amino-1-ethyl-1,2-dihydropyrazol-3-one (0.13 g, 1 mmol), prepared by the method of (A. Weisberger and A. Porter, J. Amer. Chem. Soc, (1944) 66,1849) from ethylhydrazine and ethyl cyanoacetate, 3-bromo-4-fluorobenzaldehyde (0.2 g, 1 mmol), and 1,3-cyclopentanedione (0.1 g, 1 mmol) in ethyl alcohol (2 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 0.23 g (58%) of the title compound as a tan solid. 1H NMR (300 MHz, DMSO-d6) δ 1.22 (t, 3H), 2.28 (t, 2H), 2.68 (m, 2H), 3.82 (q, 2H), 4.7 (s, 1H), 7.17 (m, 1H), 7.2 (t, 1H), 7.4 (dd,1H), 9.64 (bs, 1H), 10.4 (s, 1H); MS (ESI−) m/z 392 (M−H)−; Anal. calcd for C17H15N3BrFO2.0.5H2O: C, 50.89; H, 4.02; N, 10.47. Found: C, 50.85; H, 3.72; N, 10.25.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationthe resulting precipitate was filtered off

Sources & evidence

ORD record
ord-e776706b214648659bbfd19628915cdc
Source dataset
uspto-grants-2004_08
Patent number
US06780872B2

Reaction notes

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