Pyrrolidine → HCID 178457634, compound

HRID 448137Notes

Reaction equation

[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:6][C:7]([NH:15][C:16]([C:18]1[S:41][C:21]2[N:22](C(OCC)=O)[N:23]=[C:24]([NH:25][C:26](=[O:35])[C:27]3[CH:32]=[CH:31][C:30]([CH2:33]Cl)=[CH:29][CH:28]=3)[C:20]=2[CH:19]=1)=[O:17])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:8]>C(O)C>[CH3:8][C:7]([NH:15][C:16]([C:18]1[S:41][C:21]2[NH:22][N:23]=[C:24]([NH:25][C:26](=[O:35])[C:27]3[CH:32]=[CH:31][C:30]([CH2:33][N:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)=[CH:29][CH:28]=3)[C:20]=2[CH:19]=1)=[O:17])([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH3:6]

Participants

Conditions

Temperature: 79 °C

Procedure

Pirrolidine (1.81 mL, 21.8 mmol), was added to a suspension of ethyl 5-{[(1-methyl-1-phenylethyl)amino]carbonyl}-3-[(4-chloromethyl-benzoyl)amino]-1H-thieno[2,3-c]pyrazole-1-carboxylate (3.80 mg, 7.25 mmol) in 100 mL of dry ethanol. And the resulting mixture was stirred at 79° C. for 1 hour. Afterward the volatiles were removed by evaporation under reduced pressure and the residue was purified by chromatography over silica gel (eluant dichloromethane/methyl alcohol/aqueous ammonia 92:8:01) to give 1.2 g of the title compound.

Workup

customAfterward the volatiles were removed by evaporation under reduced pressure
customthe residue was purified by chromatography over silica gel (eluant dichloromethane/methyl alcohol/aqueous ammonia 92:8:01)

Sources & evidence

ORD record: ord-e27ac83d3c984bf2b2bf85dcd07a8aaa
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481584B2

Reaction notes

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