Triethylamine → 4-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-[2-[N-(2,5-dihydropyrrol-1-yl)amino]phenyl]piperidin-3-one

HRID 1392395Notes

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][CH:31]=[CH:30][C:29]=3[NH:34][N:35]3[CH2:39][CH:38]=[CH:37][CH2:36]3)[CH2:24][CH:23]2[OH:40])=[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][CH:31]=[CH:30][C:29]=3[NH:34][N:35]3[CH2:36][CH:37]=[CH:38][CH2:39]3)[CH2:24][C:23]2=[O:40])=[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-[2-[N-(2,5-dihydropyrrol-1-yl)amino]phenyl]piperidin-3-ol (0.7 g) obtained in Step 1 in 6 ml of dimethylsulfoxide (DMSO), was added 0.8 ml of triethylamine. The reaction mixture was cooled to 0° C. Pyridine-SO3 complex (0.75 g) was added slowly 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 0.6 g of the titled compound as white color.

Workup

additionPyridine-SO3 complex (0.75 g) was added slowly 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-0b2f34502e4a40a4a3007395a95c1ce6
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07342027B2

Reaction notes

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