HCID 66965766, compound → HCID 66965635, compound

HRID 1514975Notes

Reaction equation

HRID 1514975 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[OH:19])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([CH3:15])[CH:9]=1)=[O:6].[CH:20]([C:22]1[C:34]([CH3:35])=[CH:33][C:25]([O:26][CH2:27][C:28]([N:30]([CH3:32])[CH3:31])=[O:29])=[CH:24][C:23]=1[CH3:36])=O>CO>[CH3:15][C:10]1[CH:9]=[C:8]([NH:7][C:5]([C:4]2[CH:16]=[CH:17][C:18]3[O:19][C:20]([C:22]4[C:23]([CH3:36])=[CH:24][C:25]([O:26][CH2:27][C:28](=[O:29])[N:30]([CH3:31])[CH3:32])=[CH:33][C:34]=4[CH3:35])=[N:1][C:2]=3[CH:3]=2)=[O:6])[CH:13]=[CH:12][C:11]=1[CH3:14]

Participants

4

Reactant 2

HCID 66965766HCID 66965766, compoundHCID 86651271HCID 86651271, compound

Product 1

HCID 66965635HCID 66965635, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 3-amino-N-(3,4-dimethylphenyl)-4-hydroxy-benzamide (70 mg) and 2-(4-formyl-3,5-dimethylphenoxy)-N,N-dimethylacetamide (64 mg) in MeOH (5 mL) was stirred at 45° C. for 24 h. The MeOH was removed under reduced pressure and the residue was dissolved in CH2Cl2 (5 mL). To this solution was added DDQ (68 mg) and the dark mixture was stirred at room temperature for 6 h. The majority of the solvent was removed under reduced pressure and EtOAc was added. The solution was washed with NaHCO3 solution and water then was dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by flash chromatography using EtOAc/CH2Cl2 (1:2) as eluent to give 2-(4-dimethylcarbamoylmethoxy-2,6-dimethylphenyl)-benzooxazole-5-carboxylic acid (3,4-dimethylphenyl)-amide as a brownish solid, mp=207-209° C.; MS (m/z) 470 (M−1); 1H NMR (DMSO-d6, 400 MHz) δ 10.18 (s, 1H), 8.46 (s, 1H), 8.04 (d, J=10.36 Hz, 1H), 7.90 (d, J=8.34 Hz, 1H), 7.60 (s, 1H), 7.53 (d, J=8.08 Hz, 1H), 7.11 (d, J=8.34 Hz, 1H), 6.83 (s, 2H), 4.89 (s, 2H), 3.02 (s, 3H), 2.87 (s, 3H), 2.27 (s, 6H), 2.24 (s, 3H), 2.21 (s, 3H).

Workup

  1. customThe MeOH was removed under reduced pressure
  2. dissolutionthe residue was dissolved in CH2Cl2 (5 mL)
  3. additionTo this solution was added DDQ (68 mg)
  4. stirringthe dark mixture was stirred at room temperature for 6 h
  5. customThe majority of the solvent was removed under reduced pressure and EtOAc
  6. additionwas added
  7. washThe solution was washed with NaHCO3 solution and water
  8. dry with materialthen was dried over sodium sulfate
  9. customThe solvent was removed under reduced pressure
  10. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-65b2e232ce1b44bdb3ac2117c1400e63
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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