Dimethylformamide → HCID 86595188, compound

HRID 856792Notes

Reaction equation

HRID 856792 reaction equation
C(OCCOC1C=CC([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([CH2:25][CH:26]([CH3:28])[CH3:27])[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>C1COCC1.S(Cl)(Cl)=O>[CH2:25]([N: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)[CH:26]([CH3:28])[CH3:27]

Participants

5

Reactant 2

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

Product 1

HCID 86595188HCID 86595188, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 24386Thionyl ChlorideSolvent

Procedure

To a solution of 7-[4-(2-butoxyethoxy) phenyl]-1-isobutyl-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid (1.0 g) in THF (10 ml), thionyl chloride (0.25 ml) and DMF (1 droplet) were added at room temperature, and the mixture was stirred for 1.5 hours at room temperature. The solvent was concentrated under reduced pressure, and a solution of the residue in THF (25 ml) was added dropwise to a solution of 4-[[(1-trityl-1H-imidazol-1-yl)methyl]thio]aniline (1.13 g) in pyridine (10 ml) at 0° C. The mixture was stirred at room temperature for 20 hours, and water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was separated and purified by column chromatography (ethyl acetate:hexane 1:1), to give 7-[4-(2-butoxyethoxy) phenyl]-N-[4-[(1-trityl-1H-imidazol-4-yl) methyl]thio]phenyl]-1-isobutyl-2,3-dihydro-1H-1-benzazepine-4-carboxamide (1.43 g) as yellow crystals.

Workup

  1. concentrationThe solvent was concentrated under reduced pressure
  2. additiona solution of the residue in THF (25 ml) was added dropwise to a solution of 4-[[(1-trityl-1H-imidazol-1-yl)methyl]thio]aniline (1.13 g) in pyridine (10 ml) at 0° C
  3. stirringThe mixture was stirred at room temperature for 20 hours
  4. additionwater was added to the reaction solution
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was separated
  10. custompurified by column chromatography (ethyl acetate:hexane 1:1)

Sources & evidence

ORD record
ord-db517f4dd93740aa89a3eb34272d0389
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

Loading…