Dimethylformamide → HCID 86720683, compound

HRID 1844555Notes

Reaction equation

HRID 1844555 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]([OH:32])=O)=[C:27]([CH3:33])[C:26]=2[CH3:34])=[CH:11][CH:10]=1.[CH3:35][N:36]([CH:38]=O)[CH3:37].C(N(CC)CC)C.Cl.[CH3:48][NH:49][O:50][CH3:51]>ClCCl>[CH3:38][N:36]([CH:35]=[N:22][S:21]([C:18]1[CH:17]=[CH:16][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:49]([O:50][CH3:51])[CH3:48])=[O:32])=[C:27]([CH3:33])[C:26]=3[CH3:34])[CH:13]=2)=[CH:20][CH:19]=1)(=[O:23])=[O:24])[CH3:37]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 71203616HCID 71203616, compound

Product 1

HCID 86720683HCID 86720683, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Oxalyl chloride (0.09 g, 0.06 ml, 0.72 mmol) was added drop wise to a solution of 5-(6-methoxy-4′-sulfamoyl-[1,1′-biphenyl]-3-yl)-3,4-dimethylthiophene-2-carboxylic acid (9f, 0.16 g, 0.36 mmol) in dichloromethane (10 ml) and DMF (0.05 g, 0.06 ml, 0.72 mmol) at 0° C. The reaction mixture was 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. The residue so obtained was dissolved in dry dichloromethane (10 ml) and to this was added triethylamine (0.18 g, 0.25 ml, 1.79 mmol) followed by the addition of N,O-dimethylhydroxylamine hydrochloride (0.07 g, 0.72 mmol) under stirring. The reaction mixture was then stirred at room temperature for 2 hours. The progress of the reaction was monitored by TLC. Dichloromethane (10 mL) was added to the reaction mixture. The resultant mixture was washed with water (2×10 ml). The separated organic layer was dried over anhydrous sodium sulphate and concentrated at reduced pressure to get a crude product. The crude product so obtained was purified by column chromatography using 30% ethyl acetate in hexane as an eluent to obtain the title compound 9g (0.12 g, 65%).

Workup

  1. customto come to room temperature
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. customThe residue so obtained
  4. stirringunder stirring
  5. stirringThe reaction mixture was then stirred at room temperature for 2 hours
  6. washThe resultant mixture was washed with water (2×10 ml)
  7. dry with materialThe separated organic layer was dried over anhydrous sodium sulphate
  8. concentrationconcentrated at reduced pressure
  9. customto get a crude product
  10. customThe crude product so obtained
  11. customwas purified by column chromatography

Sources & evidence

ORD record
ord-8e5ec28cbb79421eb371232442d69f3a
Source dataset
uspto-grants-2015_02
Patent number
US08946432B2

Reaction notes

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