1,2-Dichloroethane → 5-(4-chlorophenyl)-N-methoxy-N,1,4-trimethyl-3-(4-sulfamoylphenyl)-1H-pyrrole-2-carboxamide

HRID 1053286Notes

Reaction equation

HRID 1053286 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[C:11]([C:14](O)=[O:15])=[C:10]([C:17]3[CH:22]=[CH:21][C:20]([S:23](=[O:26])(=[O:25])[NH2:24])=[CH:19][CH:18]=3)[C:9]=2[CH3:27])=[CH:4][CH:3]=1.C1C=C[C:31]2[N:36]([OH:37])N=NC=2C=1.[CH2:38](Cl)CCl.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH3:13])[C:11]([C:14]([N:36]([O:37][CH3:38])[CH3:31])=[O:15])=[C:10]([C:17]3[CH:18]=[CH:19][C:20]([S:23](=[O:25])(=[O:26])[NH2:24])=[CH:21][CH:22]=3)[C:9]=2[CH3:27])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 709126865-(4-chlorophenyl)-1,4-dimethyl-3-(4-sulfamoylphenyl)-1H-pyrrole-2-carboxylic acid

Product 1

HCID 867050305-(4-chlorophenyl)-N-methoxy-N,1,4-trimethyl-3-(4-sulfamoylphenyl)-1H-pyrrole-2-carboxamideYield 76.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 5-(4-chlorophenyl)-1,4-dimethyl-3-(4-sulfamoylphenyl)-1H-pyrrole-2-carboxylic acid (compound 49ε, 0.800 g, 1.98 mmol) in DMF (15 ml) was added HOBT (0.333 g, 2.17 mmol) at room temperature followed by the addition of N, O-dimethylhydroxylamine hydrochloride (0.386 g, 3.96 mmol). The reaction mixture was then cooled to 0° C., and to the cooled reaction mixture was added EDC (0.570 g, 2.97 mmol) and triethylamine (0.80 g, 1.10 ml, 7.92 mmol). The reaction mixture was then stirred at room temperature for 15 hr. The progress of the reaction was monitored by TLC. The reaction mixture was then concentrated under reduced pressure. The residue so obtained was taken in ethyl acetate (100 ml) and washed with saturated sodium bicarbonate solution (20 ml) followed by washing with brine (20 ml). The organic layer obtained was dried over anhydrous sodium sulphate, and concentrated under reduced pressure to obtain a crude product. The crude product was then purified by column chromatography over silica gel (100-200 mesh) using 50% ethyl acetate in hexanes as an eluent to obtain the title compound (0.680 g, 76.8%).

Workup

  1. customto the cooled reaction mixture
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. customThe residue so obtained
  4. washwashed with saturated sodium bicarbonate solution (20 ml)
  5. washby washing with brine (20 ml)
  6. customThe organic layer obtained
  7. dry with materialwas dried over anhydrous sodium sulphate
  8. concentrationconcentrated under reduced pressure
  9. customto obtain a crude product
  10. customThe crude product was then purified by column chromatography over silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-2db3ab70df524f6eb8fabad374b1e05d
Source dataset
uspto-grants-2016_07
Patent number
US09393247B2

Reaction notes

Loading…