ChemicalBook CAS DataBase List 1H-Pyrazole-3-carboxylicacid,4-amino-1-methyl-,methylester(9CI)

1H-Pyrazole-3-carboxylicacid,4-amino-1-methyl-,methylester(9CI) synthesis

4synthesis methods

Product Name:1H-Pyrazole-3-carboxylicacid,4-amino-1-methyl-,methylester(9CI)
CAS Number:637336-53-9
Molecular formula:C6H9N3O2
Molecular Weight:155.15

Methyl 1-Methyl-4-nitro-1H-pyrazole-3-carboxylate

400877-57-8

1H-Pyrazole-3-carboxylicacid,4-amino-1-methyl-,methylester(9CI)

637336-53-9

General procedure for the synthesis of methyl 1-methyl-4-aminopyrazole-3-carboxylate from ethyl 1-methyl-4-nitropyrazole-3-carboxylate: a mixture of methyl 1-methyl-4-nitro-1H-pyrazole-3-carboxylate (500 mg, 2.7 mmol) and 10% palladium carbon (50 mg) in methanol (25 mL) was placed in a Parr reactor at 60 psi of hydrogen pressure for 24 hours. Upon completion of the reaction, the mixture was filtered through a diatomaceous earth pad and washed with methanol. The filtrate was concentrated under reduced pressure to afford methyl 1-methyl-4-amino-1H-pyrazole-3-carboxylate (402 mg, 96% yield) as an off-white solid.

400877-57-8 Synthesis

400877-57-8
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$15.00/250mg

637336-53-9
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$42.00/100mg

Yield: 100%

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen in methanol at 20; for 4 h;

Steps:

70 Preparation 70: methyl 4-amino-1 -methyl-1 H-pyrazole-3-carboxylate
10% palladium/C (2.87 g, 2.7 mmol) was added to a stirred solution of methyl 1 -methyl- 4-nitro-1 H-pyrazole-3-carboxylate (p69, 7.15 g, 38.6 mmol) in methanol (250 ml_) and stirred at RT under H2 atmosphere for 4 hrs. The catalyst was filtered off and the solvent was evaporated under vacuum to afford methyl 4-amino-1 -methyl-1 H-pyrazole- 3-carboxylate (p70, 6 g, y= quant) as purple wax used as such in the next step. MS (/T7/z): 156.1 [MH]⁺

References:

CHRONOS THERAPEUTICS LIMITED;MICHELI, Fabrizio;CREMONESI, Susanna;SEMERARO, Teresa;TARSI, Luca;GIBSON, Karl Richard WO2019/81939, 2019, A1 Location in patent:Page/Page column 78

138786-86-4 Synthesis