1,2-Dichloroethane → HCID 86720684, compound

HRID 1844560Notes

Reaction equation

HRID 1844560 reaction equation
C1C=CC2N(O)N=NC=2C=1.[CH3:11][O:12][C:13]1[C:18]([C:19]2[CH:24]=[CH:23][C:22]([S:25](=[O:28])(=[O:27])[NH2:26])=[CH:21][CH:20]=2)=[CH:17][C:16]([C:29]2[N:33]([CH3:34])[C:32]([C:35](O)=[O:36])=[CH:31][C:30]=2[CH3:38])=[CH:15][CH:14]=1.Cl.[CH3:40][NH:41][O:42][CH3:43].C(Cl)CCl.C(N(CC)CC)C>CN(C=O)C>[CH3:43][O:42][N:41]([CH3:40])[C:35]([C:32]1[N:33]([CH3:34])[C:29]([C:16]2[CH:17]=[C:18]([C:19]3[CH:20]=[CH:21][C:22]([S:25](=[O:27])(=[O:28])[NH2:26])=[CH:23][CH:24]=3)[C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)=[C:30]([CH3:38])[CH:31]=1)=[O:36]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 71203601HCID 71203601, compound

Product 1

HCID 86720684HCID 86720684, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

HOBT (0.29 g, 1.92 mmol) was added to a solution of 5-(6-methoxy-4′-sulfamoyl-[1,1′-biphenyl]-3-yl)-1,4-dimethyl-1H-pyrrole-2-carboxylic acid (10c, 0.70 g, 1.75 mmol) in DMF (15 ml) under stirring at room temperature. N,O-dimethylhydroxylamine hydrochloride (0.33 g, 3.5 mmol) was then added to the reaction mixture. The reaction mixture was cooled to 0° C. and EDC (0.50 g, 2.60 mmol) and triethylamine (0.70 g, 0.97 ml, 7.00 mmol) were added to it. The reaction mixture was stirred at room temperature for 15 hours. The progress of the reaction was monitored by TLC. The reaction mixture was concentrated under reduced pressure. The residue obtained after concentration was mixed with ethyl acetate (50 ml) and the resultant mixture was washed with saturated sodium bicarbonate solution (10 ml) followed by washing with brine (10 ml). The organic layer separated was dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain a crude product. The crude product was further purified by flash column chromatography using 4% methanol in DCM as an eluent to obtain the title compound 10d (0.67 g, 87%).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. stirringThe reaction mixture was stirred at room temperature for 15 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customThe residue obtained
  5. concentrationafter concentration
  6. additionwas mixed with ethyl acetate (50 ml)
  7. washthe resultant mixture was washed with saturated sodium bicarbonate solution (10 ml)
  8. washby washing with brine (10 ml)
  9. customThe organic layer separated
  10. dry with materialwas dried over anhydrous sodium sulphate
  11. concentrationconcentrated under reduced pressure
  12. customto obtain a crude product
  13. customThe crude product was further purified by flash column chromatography

Sources & evidence

ORD record
ord-fdca23c6ff784d6bb0ab6a5ad7aa3e22
Source dataset
uspto-grants-2015_02
Patent number
US08946432B2

Reaction notes

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