HCID 22636104, compound → HCID 22636105, compound

HRID 2415715Notes

Reaction equation

HRID 2415715 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-369fc72071614ab090f95604d2c26f16
Source dataset
uspto-grants-2004_11
Patent number
US06821965B1

Reaction notes

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