3-ETHYL-1-METHYL-1H-PYRAZOLE-5-CARBOXYLIC ACID

3-ethyl-1-methylpyrazole-5-carboxylic acid ethyl ester (50 mmol) Sodium hydroxide (150 mmol), water (120 mL) and ethanol (20 mL) under reflux and stirring for 4-5 hours.The reaction solution was cooled and extracted with ethyl acetate. The resulting aqueous phase was acidified with dilute hydrochloric acid to a weak acid (pH = 5-6), and the precipitated solid was allowed to stand to give the title compound 4. 8 g.3-ethyl-1-methylpyrazole-5-carboxylic acid 3-ethyl-1-methylpyrazole-5-carboxylic acid ethyl ester (50 mmol), Sodium hydroxide (150 mmol), Water (120 mL) and ethanol (20 mL) under reflux and stirring for 4-5 hours.After the reaction solution was cooled, Ethyl acetate extraction, The resulting aqueous phase was acidified with dilute hydrochloric acid to a weak acid (pH = 5-6)Standing, Filter the precipitated solids, To give 4.8 g of the title compound.To a suspension of 6-(2-amino-5-chlorothiazol-4-yl)-3, 4-dihydroquinolin-2(1H)-one (0.100 g, 0.44 mmol) and General procedure: Pyrazole acid 9a-k (3 mmol) and thionyl chloride (7.5 mmol)were successively added to 20 mL 1, 2-dichloroethane, the mixturewere stirred under reflux for 3 h and then concentrated underreduced pressure, the crude products were added in drops into asolution of 5'a-f (5a-h) (3 mmol) and trimethylamine (6 mmol) inTHF (15 mL).The reaction mixturewas stirred under the 0 C for thenight. After reaction the mixture was poured in Na2CO3 solutionand aqueous phase was extracted with ethyl acetate (2 20 mL).The combined organic phase was washed with saturated salt water(2 20 mL), dried over anhydrous Na2SO4, and concentrated underreduced pressure and the residue was purified by silica gel columnchromatography.General procedure: Pyrazole acid 9a-k (3 mmol) and thionyl chloride (7.5 mmol)were successively added to 20 mL 1, 2-dichloroethane, the mixturewere stirred under reflux for 3 h and then concentrated underreduced pressure, the crude products were added in drops into asolution of 5'a-f (5a-h) (3 mmol) and trimethylamine (6 mmol) inTHF (15 mL).The reaction mixturewas stirred under the 0 C for thenight. After reaction the mixture was poured in Na2CO3 solutionand aqueous phase was extracted with ethyl acetate (2 20 mL).The combined organic phase was washed with saturated salt water(2 20 mL), dried over anhydrous Na2SO4, and concentrated underreduced pressure and the residue was purified by silica gel columnchromatography.General procedure: Pyrazole acid 9a-k (3 mmol) and thionyl chloride (7.5 mmol)were successively added to 20 mL 1, 2-dichloroethane, the mixturewere stirred under reflux for 3 h and then concentrated underreduced pressure, the crude products were added in drops into asolution of 5'a-f (5a-h) (3 mmol) and trimethylamine (6 mmol) inTHF (15 mL).The reaction mixturewas stirred under the 0 C for thenight. After reaction the mixture was poured in Na2CO3 solutionand aqueous phase was extracted with ethyl acetate (2 20 mL).The combined organic phase was washed with saturated salt water(2 20 mL), dried over anhydrous Na2SO4, and concentrated underreduced pressure and the residue was purified by silica gel columnchromatography.General procedure: Pyrazole acid 9a-k (3 mmol) and thionyl chloride (7.5 mmol)were successively added to 20 mL 1, 2-dichloroethane, the mixturewere stirred under reflux for 3 h and then concentrated underreduced pressure, the crude products were added in drops into asolution of 5'a-f (5a-h) (3 mmol) and trimethylamine (6 mmol) inTHF (15 mL).The reaction mixturewas stirred under the 0 C for thenight. After reaction the mixture was poured in Na2CO3 solutionand aqueous phase was extracted with ethyl acetate (2 20 mL).The combined organic phase was washed with saturated salt water(2 20 mL), dried over anhydrous Na2SO4, and concentrated underreduced pressure and the residue was purified by silica gel columnchromatography.General procedure: Pyrazole acid 9a-k (3 mmol) and thionyl chloride (7.5 mmol)were successively added to 20 mL 1, 2-dichloroethane, the mixturewere stirred under reflux for 3 h and then concentrated underreduced pressure, the crude products were added in drops into asolution of 5'a-f (5a-h) (3 mmol) and trimethylamine (6 mmol) inTHF (15 mL).The reaction mixturewas stirred under the 0 C for thenight. After reaction the mixture was poured in Na2CO3 solutionand aqueous phase was extracted with ethyl acetate (2 20 mL).The combined organic phase was washed with saturated salt water(2 20 mL), dried over anhydrous Na2SO4, and concentrated underreduced pressure and the residue was purified by silica gel columnchromatography.

Molecular Weight:154.17
XLogP3:0.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:154.074227566
Monoisotopic Mass:154.074227566
Topological Polar Surface Area:55.1
Heavy Atom Count:11
Complexity:161
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes