Hydrochloric Acid → 1-(ethoxycarbonyl)-3-[(4-chloromethyl-benzoyl)amino]-1H-thieno[2,3-c]pyrazole-5-carboxylic acid

HRID 448136Notes

Reaction equation

[Cl:1][CH2:2][C:3]1[CH:31]=[CH:30][C:6]([C:7]([NH:9][C:10]2[C:11]3[CH:22]=[C:21]([C:23]([O:25]C(C)(C)C)=[O:24])[S:20][C:12]=3[N:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:14]=2)=[O:8])=[CH:5][CH:4]=1.Cl>O1CCOCC1>[CH2:18]([O:17][C:15]([N:13]1[C:12]2[S:20][C:21]([C:23]([OH:25])=[O:24])=[CH:22][C:11]=2[C:10]([NH:9][C:7](=[O:8])[C:6]2[CH:5]=[CH:4][C:3]([CH2:2][Cl:1])=[CH:31][CH:30]=2)=[N:14]1)=[O:16])[CH3:19]

Participants

Conditions

Temperature: 50 °C

Procedure

5-tert-butyl 1-ethyl 3-[(4-chloromethyl-benzoyl)amino]-1H-thieno[2,3-c]pyrazole-1,5-dicarboxylate (8.2 g) was added to a solution of hydrochloric acid in dioxane (88 mL, 4N solution). The resulting mixture was stirred at 50° C. for 2 hours. Afterward, volatiles were removed by evaporation under reduced pressure and the residue triturated with diethyl ether, filtered, extensively washed with diethyl ether and dried under vacuum at 40° C. to give 5.7 g of the title compound, used in the next step without further purification.

Workup

customAfterward, volatiles were removed by evaporation under reduced pressure
customthe residue triturated with diethyl ether
filtrationfiltered
washextensively washed with diethyl ether
customdried under vacuum at 40° C.

Sources & evidence

ORD record: ord-42bf2832a7e04b17adef2c927885a8e9
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481584B2

Reaction notes

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