HCID 22636104, compound → HCID 22636105, compound

HRID 502042Notes

Reaction equation

HRID 502042 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:37]=[CH:38][CH:39]=1)[C:12]([NH:14][C:15]1[CH:16]=[C:17]([CH:33]=[CH:34][C:35]=1[CH3:36])[C:18]([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[CH:22]=1)=[O:19])=[O:13])C1C=CC=CC=1>[Pd].C(OCC)(=O)C>[OH:8][C:9]1[CH:10]=[C:11]([CH:37]=[CH:38][CH:39]=1)[C:12]([NH:14][C:15]1[CH:16]=[C:17]([CH:33]=[CH:34][C:35]=1[CH3:36])[C:18]([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([N:27]2[CH2:28][CH2:29][O:30][CH2:31][CH2:32]2)[CH:22]=1)=[O:19])=[O:13]

Participants

4

Reactant 1

HCID 22636104HCID 22636104, compound

Product 1

HCID 22636105HCID 22636105, compoundYield 80.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-(3-benzyloxybenzamido)-4-methyl-N-(3-morpholinophenyl)benzamide (4.49 g), 10% palladium-on-carbon (0.5 g) and ethyl acetate was stirred under an atmosphere of hydrogen gas for 12 hours. The resultant mixture was filtered through diatomaceous earth and the separated solids were washed with warm DMF (200 ml). The combined filtrates were concentrated to a volume of about 20 ml and water (50 ml) was added. The resultant solid was dried under vacuum at 55° C. There was thus obtained the title compound as a solid (2.99 g); NMR Spectrum: (DMSOd6) 2.25 (s, 3H), 3.07 (t, 4H), 3.72 (t, 4H), 6.67 (m, 1H), 6.97 (m, 1H), 7.18 (t, 1H), 7.36 (m, 6H), 7.78 (m, 1H), 7.92 (s, 1H), 9.68 (s, 1H), 9.89 (s, H), 10.01 (s, 1H); Mass Spectrum: M+H+ 432.

Workup

  1. filtrationThe resultant mixture was filtered through diatomaceous earth
  2. washthe separated solids were washed with warm DMF (200 ml)
  3. concentrationThe combined filtrates were concentrated to a volume of about 20 ml and water (50 ml)
  4. additionwas added
  5. customThe resultant solid was dried under vacuum at 55° C

Sources & evidence

ORD record
ord-d7941dd98f65403a969a73730331f3ca
Source dataset
uspto-grants-2010_08
Patent number
US07772432B2

Reaction notes

Loading…