Dimethylformamide → HCID 86720680, compound

HRID 1844542Notes

Reaction equation

HRID 1844542 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([S:21](=[O:24])(=[O:23])[NH2:22])=[CH:17][CH:16]=2)=[CH:13][C:12]([C:25]2[S:29][C:28]([C:30](O)=[O:31])=[CH:27][C:26]=2[CH3:33])=[CH:11][CH:10]=1.[CH3:34][N:35]([CH:37]=O)[CH3:36].C(N(CC)CC)C.Cl.[CH3:47][NH:48][O:49][CH3:50]>ClCCl>[CH3:37][N:35]([CH:34]=[N:22][S:21]([C:18]1[CH:19]=[CH:20][C:15]([C:14]2[C:9]([O:8][CH3:7])=[CH:10][CH:11]=[C:12]([C:25]3[S:29][C:28]([C:30]([N:48]([O:49][CH3:50])[CH3:47])=[O:31])=[CH:27][C:26]=3[CH3:33])[CH:13]=2)=[CH:16][CH:17]=1)(=[O:24])=[O:23])[CH3:36]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 71203600HCID 71203600, compound

Product 1

HCID 86720680HCID 86720680, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (0.87 g, 0.58 ml, 6.94 mmol) was added drop wise to a solution of 5-(6-methoxy-4′-sulfamoyl-[1,1′-biphenyl]-3-yl)-4-methylthiophene-2-carboxylic acid (1c, 1.4 g, 3.47 mmol) in dichloromethane (28 ml) and DMF (0.53 ml, 6.94 mmol) at 0° C. The reaction mixture was then allowed to come to room temperature and stirred for 1.5 hr under nitrogen atmosphere. The progress of the reaction was monitored by TLC. The reaction mixture was then concentrated under reduced pressure and used directly for further reaction. Residue obtained after concentration was dissolved in dry dichloromethane (20 ml) and to this was added triethylamine (2.1 g, 2.89 ml, 20.8 mmol) followed by the addition of N,O-dimethylhydroxylamine hydrochloride (1.34 g, 13.88 mmol) under stirring. The reaction mixture was stirred at room temperature for 2 hours. The progress of the reaction was monitored by TLC. The reaction mixture was then diluted with dichloromethane (100 ml). The mixture obtained was washed with water (2×20 ml), followed by washing with brine (1×20 ml). The separated organic layer was dried over anhydrous sodium sulphate, and concentrated under reduced pressure to obtain a crude product. The crude product was further purified by column chromatography over silica gel using 80% ethyl acetate in hexane as an eluent to obtain the title compound (1.1 g, 63.2%).

Workup

  1. customto come to room temperature
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. customused directly for further reaction
  4. customResidue obtained
  5. concentrationafter concentration
  6. dissolutionwas dissolved in dry dichloromethane (20 ml)
  7. stirringunder stirring
  8. stirringThe reaction mixture was stirred at room temperature for 2 hours
  9. customThe mixture obtained
  10. washwas washed with water (2×20 ml)
  11. washby washing with brine (1×20 ml)
  12. dry with materialThe separated organic layer was dried over anhydrous sodium sulphate
  13. concentrationconcentrated under reduced pressure
  14. customto obtain a crude product
  15. customThe crude product was further purified by column chromatography over silica gel using 80% ethyl acetate in hexane as an eluent

Sources & evidence

ORD record
ord-0326b9a689e04b32b7747132f07a4753
Source dataset
uspto-grants-2015_02
Patent number
US08946432B2

Reaction notes

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