Triethylamine → 4-[N-[1-[N-(furan-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-[4-fluoro-2-(pyrrol-1-yl)phenyl]piperidin-3-one

HRID 1392421Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To the solution of 4-[N-[1-[N-(furan-2-ylcarbonyl)amino]cyclohexane carbonyl]amino]-1-[4-fluoro-2-(pyrrol-1-yl)phenyl]piperidin-3-ol (1.8 g) obtained in Step 1 in 10 ml of dimethylsulfoxide, was added 2 ml of triethylamine. The reaction mixture was cooled to 0° C. Pyridine-SO3 complex (1.8 g) was added to the reaction mixture, which was then stirred for about 2 hours at room temperature. The reaction mixture was diluted with 50 ml of ethyl acetate and washed with brine. The resulting organic layer was dried and concentrated on sodium sulfate. The resulting residue was filtered and dried to give 1.5 g of the titled compound as white color.

Workup

additionPyridine-SO3 complex (1.8 g) was added to the reaction mixture, which
washwashed with brine
customThe resulting organic layer was dried
concentrationconcentrated on sodium sulfate
filtrationThe resulting residue was filtered
customdried

Sources & evidence

ORD record: ord-a3ff85b0f9e04d999d04ce1fb72dbf86
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07342027B2

Reaction notes

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