ethyl 5-{[(1-methyl-1-phenylethyl)amino]carbonyl}-3-[(4-morpholin-4-ylbenzoyl)amino]-1H-thieno[2,3-c]pyrazole-1-carboxylate → HCID 178457636, compound

HRID 448132Notes

Reaction equation

[CH3:1][C:2]([NH:10][C:11]([C:13]1[S:40][C:16]2[N:17](C(OCC)=O)[N:18]=[C:19]([NH:20][C:21](=[O:34])[C:22]3[CH:27]=[CH:26][C:25]([N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[CH:24][CH:23]=3)[C:15]=2[CH:14]=1)=[O:12])([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:3]>CO.C(N(CC)CC)C>[CH3:3][C:2]([NH:10][C:11]([C:13]1[S:40][C:16]2[NH:17][N:18]=[C:19]([NH:20][C:21](=[O:34])[C:22]3[CH:27]=[CH:26][C:25]([N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[CH:24][CH:23]=3)[C:15]=2[CH:14]=1)=[O:12])([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH3:1]

Participants

Conditions

Temperature: 70 °C

Procedure

A suspension of ethyl 5-{[(1-methyl-1-phenylethyl)amino]carbonyl}-3-[(4-morpholin-4-ylbenzoyl)amino]-1H-thieno[2,3-c]pyrazole-1-carboxylate (3.71 g, 6.6 mmol) in methanol (MeOH, 70 mL) and triethylamine (TEA, 7 mL) was stirred at 70° C. for 5 hours. After evaporation of the solvent under reduced pressure, the residue was taken up with DCM and washed with water. The organic layer was separated, dried over sodium sulfate and evaporated. Purification by chromatography (DCM/MeOH 47:3) gave 2.8 g of the title compound.

Workup

customAfter evaporation of the solvent under reduced pressure
washwashed with water
customThe organic layer was separated
dry with materialdried over sodium sulfate
customevaporated
customPurification by chromatography (DCM/MeOH 47:3)

Sources & evidence

ORD record: ord-08272b04f3f44b5ba8e275b3730bd6e6
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481584B2

Reaction notes

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