Dimethylformamide → HCID 178500174, compound

HRID 1360781Notes

Reaction equation

HRID 1360781 reaction equation
OOS([O-])=O.[K+].[CH3:7][O:8][C:9](=[O:24])[C:10]([CH3:23])([CH3:22])[CH2:11][C:12]1[CH:17]=[C:16]([CH3:18])[C:15]([CH:19]=O)=[C:14]([CH3:21])[CH:13]=1.ClC1C=C(N[C:33]2[O:37][C:36]([C:38]3[CH:39]=[CH:40][C:41]4[N:45]=C(C5C(C)=CC(CCC(O)=O)=CC=5C)[NH:43][C:42]=4[CH:59]=3)=[N:35][N:34]=2)C=CC=1.CN([CH:63]=[O:64])C>O>[CH3:7][O:8][C:9](=[O:24])[C:10]([CH3:23])([CH3:22])[CH2:11][C:12]1[CH:17]=[C:16]([CH3:18])[C:15]([C:19]2[NH:45][C:41]3[CH:40]=[CH:39][C:38]([C:36]4[O:37][C:33]([C:12]5[CH:17]=[CH:16][C:15]([O:64][CH3:63])=[CH:14][CH:13]=5)=[N:34][N:35]=4)=[CH:59][C:42]=3[N:43]=2)=[C:14]([CH3:21])[CH:13]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 23707502Potassium hydroxy sulfiteHCID 252105913-(4-{6-[5-(3-Chlorophenylamino)-[1,3,4]oxadiazol-2-yl]-1H-benzoimidazol-2-yl}-3,5-dimethylphenyl)-propionic acidHCID 86632822Methyl 3-(4-formyl-3,5-dimethylphenyl)-2,2-dimethylpropanoate

Product 1

HCID 178500174HCID 178500174, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Oxone (420 mg, 0.683 mmol) was added to a mixture of 3-(4-formyl-3,5-dimethyl-phenyl)-2,2-dimethyl-propionic acid methyl ester (250 mg, 1.00 mmol) and 4-[5-(4-Methoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-benzene-1,2-diamine (prepared as described in Example 1-59, 300 mg, 1.06 mmol) in DMF (8 mL) and water (0.8 mL), and the mixture was stirred at room temperature for 18 h. The mixture was partitioned between EtOAc and water. The EtOAc extract was washed with brine, dried over Na2SO4, concentrated and chromatographed to give the title compound. m/z 511.3 (MH+).

Workup

  1. customThe mixture was partitioned between EtOAc and water
  2. extractionThe EtOAc extract
  3. washwas washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customchromatographed

Sources & evidence

ORD record
ord-cb1966aa095c43a7b760958a6abbfdb6
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

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