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CAS No. : | 1041481-59-7 | MDL No. : | MFCD11007930 |
Formula : | C8H5FN2O2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | CLNSDURQQKBHKP-UHFFFAOYSA-N |
M.W : | 180.14 | Pubchem ID : | 22260727 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; DMF (N,N-dimethyl-formamide); for 0.75h; | To 1.65 g of 4-fluoro-1H-indazole-5-carbonitrile obtained by Production example 85, 8 mL of glacial acetic acid, 8 mL of water and 16 mL of concentrated sulfuric acid were added and stirred at 110C for 4 hours. After allowing the reaction solution to cool, 150 mL of ice water was added, and the precipitated carboxylic acid was collected by filtration. Under ice cooling, to a solution of the obtained carboxylic acid in N,N-dimethylformamide 12 mL-tetrahydrofuran 40 mL, a solution containing excess diazomethane in diethyl ether was added, and stirred at this temperature for 45 minutes. After distilling off the solvent under reduced pressure, the residue was dissolved in 100 mL of ethyl acetate, washed successively with saturated aqueous sodium hydrogen carbonate, water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, to afford 1.98 g of the title compound as bright yellow crystals.1H-NMR ( 400 MHz, DMSO-D6 ) delta 3.87 ( 3H, s ), 7.45 ( 1H, d, J = 8.8 Hz ), 7.82 ( 1H, dd, J = 6.8, 8.8 Hz ), 8.36 ( 1H, s ), 13.70 ( 1H, s ) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid; water; acetic acid; at 110.0℃; for 4.0h; | To 1.65 g of 4-fluoro-1H-indazole-5-carbonitrile obtained by Production example 85, 8 mL of glacial acetic acid, 8 mL of water and 16 mL of concentrated sulfuric acid were added and stirred at 110C for 4 hours. After allowing the reaction solution to cool, 150 mL of ice water was added, and the precipitated carboxylic acid was collected by filtration. Under ice cooling, to a solution of the obtained carboxylic acid in N,N-dimethylformamide 12 mL-tetrahydrofuran 40 mL, a solution containing excess diazomethane in diethyl ether was added, and stirred at this temperature for 45 minutes. After distilling off the solvent under reduced pressure, the residue was dissolved in 100 mL of ethyl acetate, washed successively with saturated aqueous sodium hydrogen carbonate, water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, to afford 1.98 g of the title compound as bright yellow crystals.1H-NMR ( 400 MHz, DMSO-D6 ) delta 3.87 ( 3H, s ), 7.45 ( 1H, d, J = 8.8 Hz ), 7.82 ( 1H, dd, J = 6.8, 8.8 Hz ), 8.36 ( 1H, s ), 13.70 ( 1H, s ) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20.0℃; for 24.0h; | Step 1:400 mg of <strong>[1041481-59-7]4-fluoro-1H-indazole-5-carboxylic acid</strong>, 470 mg of 4-(3-methoxybenzyl)thiosemicarbazide and 468 mg of DAPECI are stirred for 24 hours at RT in 5 ml of DMF. The batch is poured into 1 N hydrochloric acid, and the resultant precipitate is filtered off with suction and dried, giving 410 mg of product [49%, MS-FAB (M+H+)=374.1; Rf (polar method): 1.69 min], which is employed in step 2 without further purification. |
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