Dimethylformamide → HCID 69521870, compound

HRID 586914Notes

Reaction equation

HRID 586914 reaction equation
C(OCCOC1C=CC([C:15]2[CH:16]=[CH:17][C:18]3[N:24](C4C=CC(S(=O)(=O)NC)=CC=4)[CH2:23][CH2:22][C:21]([C:36](O)=[O:37])=[CH:20][C:19]=3[CH:39]=2)=CC=1)CCC.C(Cl)(=O)C(Cl)=O.C[N:47](C=O)C>C1COCC1>[NH:24]1[C:18]2[CH:17]=[CH:16][CH:15]=[CH:39][C:19]=2[CH:20]=[C:21]([C:36]([NH2:47])=[O:37])[CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 22328925HCID 22328925, compound

Product 1

HCID 69521870HCID 69521870, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In THF (7 ml) was dissolved 7-[4-(2-butoxyethoxy)phenyl]-1-(N-methyl-4-sulfamoylphenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid (0.4 g). Under ice-cooling, to the solution were added oxalyl chloride (0.19 ml) and DMF (catalytic amount). The mixture was stirred at room temperature for 1 hour, and the solvent was evaporated under reduced pressure. In THF (25 ml) was dissolved the residue, and the solution was added dropwise to a suspension of 4-[N-methyl-N-(tetrahydro-2H-pyran-4-yl)aminomethyl]aniline dihydrochloride (0.28 g) and triethylamine (0.5 ml) in THF (5 ml), under ice-cooling. The mixture was stirred at room temperature under nitrogen atmosphere for 1 hour and the solvent was evaporated under reduced pressure. To the residue was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried with anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified with basic silica gel column chromatography (ethyl acetate) to give crude crystals, which were recrystallized from ethyl acetate-hexane to give 7-[4-(2-butoxyethoxy)phenyl]-1-(N-methyl-4-sulfamoylphenyl)-N-[4-[[N-methyl-N-tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide (Compound 48) (0.28 g) as pale yellow crystals.

Workup

  1. temperatureUnder ice-cooling, to the solution
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionIn THF (25 ml) was dissolved the residue
  4. additionthe solution was added dropwise to a suspension of 4-[N-methyl-N-(tetrahydro-2H-pyran-4-yl)aminomethyl]aniline dihydrochloride (0.28 g) and triethylamine (0.5 ml) in THF (5 ml), under ice-
  5. temperaturecooling
  6. stirringThe mixture was stirred at room temperature under nitrogen atmosphere for 1 hour
  7. customthe solvent was evaporated under reduced pressure
  8. additionTo the residue was added water
  9. extractionthe mixture was extracted with ethyl acetate
  10. washThe organic layer was washed with water and saturated brine
  11. dry with materialdried with anhydrous magnesium sulfate
  12. customThe solvent was evaporated
  13. customthe residue was purified with basic silica gel column chromatography (ethyl acetate)
  14. customto give crude crystals, which
  15. customwere recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-b7a222522f4b475d9e2aceea4214c89b
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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