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

HRID 1392383
Notes
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Reaction equation

HRID 1392383 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 115679944-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-3-piperidinol hydrochlorideHCID 693117581-Flourophenyl methyl sulfone

Product 1

HCID 116710854-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(2-methylsulfonylphenyl)piperidin-3-olYield 38.3%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 8857Ethyl AcetateSolvent

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

  1. temperaturecooled to room temperature
  2. washwashed with brine
  3. customThe resulting organic layer was dried
  4. concentrationconcentrated on sodium sulfate
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes