Dimethylformamide → HCID 69521870, compound

HRID 856508Notes

Reaction equation

HRID 856508 reaction equation
C(OCCOC1C=CC([C:15]2[CH:16]=[CH:17][C:18]3[N:24](CC(C)C)[CH2:23][CH2:22][C:21]([C:29](O)=[O:30])=[CH:20][C:19]=3[CH:32]=2)=CC=1)CCC.C[N:34](C=O)C.S(Cl)(Cl)=O>C1COCC1>[NH:24]1[C:18]2[CH:17]=[CH:16][CH:15]=[CH:32][C:19]=2[CH:20]=[C:21]([C:29]([NH2:34])=[O:30])[CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 223289057-[4-(2-Butoxyethoxy)phenyl]-1-isobutyl-2,3-dihydro-1-benzazepine-4-carboxylic acid

Product 1

HCID 69521870HCID 69521870, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-2,3-dihydro-1-benzazepine-4-carboxylic acid (0.80 g) was dissolved in THF (8.0 ml), DMF (3 droplets) was added to the mixture, thionyl chloride (0.20 ml) was added to the mixture, and the mixture was stirred for 1 hour at room temperature. The solvent was removed under reduced pressure, and a solution of the obtained residue in THF (16 ml) was added dropwise to a solution of N-methyl-N-[(1-propylimidazol-2-yl)methyl]-1,4-benzodiamine (0.38 g) and triethylamine (2.04 ml) in THF (7.6 ml) under ice-cooling and the mixture was stirred for 2 hours at room temperature. The reaction solution was added to water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give 7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-N-[4-[methyl[(1-propylimidazol-2-yl)methyl]]amino]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide (Compound 264) (0.92 g).

Workup

  1. additionwas added to the mixture
  2. customThe solvent was removed under reduced pressure
  3. additiona solution of the obtained residue in THF (16 ml) was added dropwise to a solution of N-methyl-N-[(1-propylimidazol-2-yl)methyl]-1,4-benzodiamine (0.38 g) and triethylamine (2.04 ml) in THF (7.6 ml) under ice-
  4. temperaturecooling
  5. stirringthe mixture was stirred for 2 hours at room temperature
  6. additionThe reaction solution was added to water
  7. extractionextracted with ethyl acetate
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried over magnesium sulfate
  10. customThe solvent was removed under reduced pressure
  11. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a7db858f62ad472195084fc947deb656
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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