Triethylamine → HCID 86705024, compound

HRID 1518685Notes

Reaction equation

HRID 1518685 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][C:8]1[C:9]([C:22]2[CH:27]=[CH:26][C:25]([S:28](=[O:31])(=[O:30])[NH2:29])=[CH:24][CH:23]=2)=[C:10]([C:19]([OH:21])=O)[S:11][C:12]=1[N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.[CH2:32]([N:34]([CH2:37]C)[CH2:35]C)C.Cl.[CH3:40][NH:41][O:42][CH3:43]>ClCCl.CN(C=O)C>[CH3:32][N:34]([CH:37]=[N:29][S:28]([C:25]1[CH:24]=[CH:23][C:22]([C:9]2[C:8]([CH3:7])=[C:12]([N:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)[S:11][C:10]=2[C:19]([N:41]([O:42][CH3:43])[CH3:40])=[O:21])=[CH:27][CH:26]=1)(=[O:30])=[O:31])[CH3:35]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 68285311HCID 68285311, compound2×

Product 1

HCID 86705024HCID 86705024, compoundYield 53.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (0.19 g, 0.13 ml, 1.49 mmol) was added dropwise at 0° C. to a solution of 4-methyl-5-morpholino-3-(4-sulfamoylphenyl)thiophene-2-carboxylic acid (compound 24e, 0.19 g, 0.497 mmol) in a mixture of dichloromethane (15 ml) and DMF (0.073 g, 0.08 ml, 0.99 m mol). The resulting mixture was allowed to warm to room temperature and stirred for 1.5 hr, under a nitrogen atmosphere. The progress of the reaction was monitored by TLC. The reaction mixture was concentrated under reduced pressure and used directly for further reaction. The residue so obtained was dissolved in dry dichloromethane (15 ml) and to this was added triethylamine (0.251 g, 0.35 ml, 2.48 mmol) followed by the addition of N,O-dimethylhydroxylamine hydrochloride (0.098 g, 0.99 mmol) under stirring at 0° C. The reaction mixture was stirred at room temperature for 2 hr. The progress of reaction was monitored by TLC. The reaction mixture was washed with water (2×10 ml) and the resulting 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 (100-200 mesh) using 1% methanol in dichloromethane as an eluent to obtain the title compound (0.127 g, 53%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customused directly for further reaction
  3. customThe residue so obtained
  4. stirringunder stirring at 0° C
  5. stirringThe reaction mixture was stirred at room temperature for 2 hr
  6. customThe progress of reaction
  7. washThe reaction mixture was washed with water (2×10 ml)
  8. dry with materialthe resulting organic layer was dried over anhydrous sodium sulphate
  9. concentrationconcentrated under reduced pressure
  10. customto obtain a crude product
  11. customThe crude product was further purified by column chromatography over silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-e550a3b910084d839c5fcef264bfb9d0
Source dataset
uspto-grants-2015_07
Patent number
US09072731B2

Reaction notes

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