Uses
1H-Pyrazole-3-carboxaldehyde is an intermediate used to prepare fused pyrrole carboxylic acids as novel, potent D-amino acid oxidase (DAO) inhibitors. It is also a building block to synthesize α-substituted benzylidenemalononitrile tyrphostins as potent inhibitors of EGF receptor and ErbB2/neu tyrosine kinases.
Synthesis
The general procedure for the synthesis of 3-pyrazolecarboxaldehyde from 3-dimethoxymethyl-1H-pyrazole: 2.3 kg of formic acid was added slowly and dropwise to 15.5 kg of an aqueous solution containing 13.8 kg of 3-dimethoxymethyl-1H-pyrazole at 0-15 °C. Subsequently, the reaction mixture was magnetically stirred at 25 °C for 12 h. A light yellow solid was obtained upon completion of the reaction. The precipitate was separated by filtration and the filter cake was washed with 10 L of water to give 643 g of the final yellow solid product 3-pyrazolecarboxaldehyde.
References
[1] Journal of Organic Chemistry, 2007, vol. 72, # 15, p. 5890 - 5893
[2] Chinese Journal of Catalysis, 2016, vol. 37, # 9, p. 1446 - 1450
[3] European Journal of Medicinal Chemistry, 1993, vol. 28, # 2, p. 129 - 140
[4] Patent: CN107235982, 2017, A. Location in patent: Paragraph 0008
