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 1096158Notes

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-7fcf0f38faa048b7aef681ca041ff388
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138217B2

Reaction notes

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