Potassium Carbonate → 4-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(2-methylsulfonylphenyl)piperidin-3-ol

HRID 1392383Notes

Reaction equation

Cl.[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH:4]=[C:3]1[C:11]([NH:13][C:14]1([C:20]([NH:22][CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH:24]2[OH:29])=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:12].[CH3:30][S:31]([C:34]1(F)[CH:39]=[CH:38][CH:37]=[CH:36][CH2:35]1)(=[O:33])=[O:32].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH:4]=[C:3]1[C:11]([NH:13][C:14]1([C:20]([NH:22][CH:23]2[CH2:28][CH2:27][N:26]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=3[S:31]([CH3:30])(=[O:33])=[O:32])[CH2:25][CH:24]2[OH:29])=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:12]

Participants

Conditions

Temperature: 100 °C

Procedure

To the solution of 4-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-3-piperidinol hydrochloride (10 g, 23.7 mmol) obtained in Step 2 and 1-flourophenyl methyl sulfone (4.9 g, 28.4 mmol) in 50 ml of dimethylformamide, was added potassium carbonate (8.2 g, 59.3 mmol). The reaction mixture was stirred overnight at about 100° C., cooled to room temperature, diluted with 200 ml of ethyl acetate, and washed with brine. The resulting organic layer was dried and concentrated on sodium sulfate. The resulting residue was purified with column chromatography to give 4.9 g of the titled compound as white solid.

Workup

temperaturecooled to room temperature
washwashed with brine
customThe resulting organic layer was dried
concentrationconcentrated on sodium sulfate
customThe resulting residue was purified with column chromatography

Sources & evidence

ORD record: ord-eb097e5d20ef40349b115370eae21fc8
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07342027B2

Reaction notes

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