Dimethylformamide → HCID 86720685, compound

HRID 1844561Notes

Reaction equation

HRID 1844561 reaction equation
[CH3:1][N:2]([CH:4]=O)[CH3:3].[CH3:6][O:7][N:8]([CH3:36])[C:9]([C:11]1[N:12]([CH3:35])[C:13]([C:17]2[CH:18]=[C:19]([C:25]3[CH:30]=[CH:29][C:28]([S:31](=[O:34])(=[O:33])[NH2:32])=[CH:27][CH:26]=3)[C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)=[C:14]([CH3:16])[CH:15]=1)=[O:10]>C(OCC)(=O)C>[CH3:1][N:2]([CH:4]=[N:32][S:31]([C:28]1[CH:29]=[CH:30][C:25]([C:19]2[C:20]([O:23][CH3:24])=[CH:21][CH:22]=[C:17]([C:13]3[N:12]([CH3:35])[C:11]([C:9]([N:8]([O:7][CH3:6])[CH3:36])=[O:10])=[CH:15][C:14]=3[CH3:16])[CH:18]=2)=[CH:26][CH:27]=1)(=[O:33])=[O:34])[CH3:3]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 86720684HCID 86720684, compound

Product 1

HCID 86720685HCID 86720685, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

DMF (0.65 ml) and DMF acetal (0.19 g, 0.21 ml, 1.61 mmol) were added to a solution of N-methoxy-5-(6-methoxy-4′-sulfamoyl-[1,1′-biphenyl]-3-yl)-N,1,4-trimethyl-1H-pyrrole-2-carboxamide (10d, 0.65 g, 1.46 mmol) in ethyl acetate (13 ml) under stirring at room temperature. The mixture was stirred at room temperature for 15 hr under nitrogen atmosphere. The progress of the reaction was monitored by TLC. The reaction mixture was diluted with ethyl acetate (50 ml) and the mixture so obtained was washed with water (2×20 ml). The organic layer separated was dried over Na2SO4 and concentrated to obtain a crude product. The crude product was purified by flash column chromatography using 4% methanol in DCM as an eluent to obtain the title compound 10e (0.62 g, 84.9%).

Workup

  1. stirringThe mixture was stirred at room temperature for 15 hr under nitrogen atmosphere
  2. customthe mixture so obtained
  3. washwas washed with water (2×20 ml)
  4. customThe organic layer separated
  5. dry with materialwas dried over Na2SO4
  6. concentrationconcentrated
  7. customto obtain a crude product
  8. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-9df7a362bd3441cfb36d0282896e4065
Source dataset
uspto-grants-2015_02
Patent number
US08946432B2

Reaction notes

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