HCID 67487860, compound → HCID 67487637, compound

HRID 2371249Notes

Reaction equation

HRID 2371249 reaction equation
[O:1]1[C:6]2=[CH:7][CH:8]=[CH:9][C:5]2=[CH:4][CH:3]=[C:2]1[N:10]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:11]([CH:13]([C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]=2)=[CH:26][CH:25]=1)[CH2:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=1)=[O:12]>CCO.[Pd]>[O:1]1[C:6]2=[CH:7][CH:8]=[CH:9][C:5]2=[CH:4][CH:3]=[C:2]1[N:10]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:11]([CH:13]([C:24]1[CH:25]=[CH:26][C:27]([CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)=[CH:28][CH:29]=1)[CH2:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=1)=[O:12]

Participants

4

Reactant 1

HCID 67487860HCID 67487860, compound

Product 1

HCID 67487637HCID 67487637, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of 4-[2-(4-benzofuran-2yl-phenylcarbamoyl)-2-(4-cyclohex-1-enyl-phenyl)-ethyl]-benzoic acid (Example 1.003, Step F) (0.23 g, 0.42 mmol) in EtOH (15 mL) at room temperature, was added 10% Pd/C (30 mg) and hydrogenated under 1 atm. H2 (gas) for a 3 h period. The reaction mixture was filtered through a celite plug, washed with ethyl acetate (2×50 mL) and concentrated under reduced pressure. The resulting compound was dried under vacuum to afford 4-[2-(4-benzofuran-2yl-phenylcarbamoyl)-2-(4-cyclohexyl-phenyl)-ethyl]-benzoic acid (9) (0.21 g, 92%), 1H NMR (300 MHz, CD3OD): 7.85 (d, J=8.1 Hz, 2H), 7.70 (d, J=8.7 Hz, 2H), 7.50 (d, J=9.0 Hz, 2H), 7.16-7.45 (m, 8H), 7.07 (s, 1H), 3.95 (dd, J=6.0, 9.3 Hz, 1H), 3.51 (dd, J=9.3, 12.0 Hz, 1H), 3.06 (dd, J=5.7, 10.8 Hz, 1H), 2.42-2.48 (m, 1H), 1.72-1.90 (m, 5H), 1.35-1.46 (m, 5H); LC-MS m/z=543 [C37H36NO3+H]+

Workup

  1. filtrationThe reaction mixture was filtered through a celite plug
  2. washwashed with ethyl acetate (2×50 mL)
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting compound was dried under vacuum

Sources & evidence

ORD record
ord-63570a84925246859b4ef1257c91dc1e
Source dataset
uspto-grants-2014_04
Patent number
US08710236B2

Reaction notes

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