Triethylamine → 4-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(4-fluoro-2-trifluoromethylphenyl)piperidin-3-one

HRID 1392386Notes

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C:13]1([C:19]([NH:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=3[C:35]([F:38])([F:37])[F:36])[CH2:24][CH:23]2[OH:39])=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:11].C(N(CC)CC)C>CS(C)=O.C(OCC)(=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C:13]1([C:19]([NH:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=3[C:35]([F:37])([F:38])[F:36])[CH2:24][C:23]2=[O:39])=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:11]

Participants

Conditions

Temperature: 0 °C

Procedure

To the solution of 4-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(4-fluoro-2-trifluoromethylphenyl)piperidin-3-ol (0.15 g) obtained in Step 1 in 3 ml of dimethyl sulfoxide (DMSO), was added 0.16 ml of triethylamine. The reaction mixture was cooled to 0° C. Pyridine-SO3 complex (0.15 g) was added slowly to the reaction mixture, which was then stirred for about 4 hours at room temperature, diluted with 20 ml of ethyl acetate, washed with brine, and dried and concentrated. The resulting residue was purified with column chromatography to give 84 mg of the titled compound as white solid.

Workup

additionPyridine-SO3 complex (0.15 g) was added slowly to the reaction mixture, which
washwashed with brine
customdried
concentrationconcentrated
customThe resulting residue was purified with column chromatography

Sources & evidence

ORD record: ord-6f9772fb26b64925867c541a0973e623
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07342027B2

Reaction notes

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