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ChemicalBook CAS DataBase List Sildenafil Impurity 13
76424-56-1

Sildenafil Impurity 13 synthesis

5synthesis methods
139756-08-4 Synthesis
4-Nitro-3-propyl-1H-pyrazole-5-carboxamide

139756-08-4
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Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

1000210-73-0
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Yield: 36%

Reaction Conditions:

with sodium borohydrid;palladium in methanol;water

Steps:

37 4-Amino-3-n-propylpyrazole-5-carboxamide
EXAMPLE 37 4-Amino-3-n-propylpyrazole-5-carboxamide A solution of 4-nitro-3-n-propylpyrazole-5-carboxamide (198 mg, 1.0 mmol) in methanol (5 ml) was added dropwise to a mixture of sodium borohydride (113 mg, 2.97 mmol), 10% palladium on carbon (5 mg) and water (3 ml). The mixture was stirred at room temperature for 3 hours, filtered and the solvent removed by evaporation under vacuum. Crystallisation of the residue from ethyl acetate-methanol gave the title compound as an off-white solid (61 mg, 36%), m.p. 196°-201° C. Rf 0.4 (silica; dichloromethane, methanol, ammonium hydroxide; 90:10:1). Found: C,48.96; H,6.98; N,32.08. C7 H12 N4 O requires C,49.98; H,7.19; N,33.31%.

References:

Pfizer Inc. US5250534, 1993, A