Pyridine → HCID 19706883, compound

HRID 726703Notes

Reaction equation

HRID 726703 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[C:12](=[O:19])[C:11]([F:21])([F:20])[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:30]1([C:36]2[CH:44]=[CH:43][CH:42]=[CH:41][C:37]=2[C:38](Cl)=[O:39])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(Cl)Cl>[F:20][C:11]1([F:21])[C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N:8]([C:6](=[O:7])[C:5]2[CH:22]=[CH:23][C:2]([NH:1][C:38](=[O:39])[C:37]3[CH:41]=[CH:42][CH:43]=[CH:44][C:36]=3[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[CH:3][CH:4]=2)[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 10567395HCID 10567395, compoundHCID 12563768[1,1'-Biphenyl]-2-carbonyl chloride

Product 1

HCID 19706883HCID 19706883, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-(4-Aminobenzoyl)-4,4-difluoro-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one (200 mg) and 5 ml of pyridine were dissolved in 10 ml of methylene chloride, and 10 ml of a methylene chloride solution containing the o-phenylbenzoic acid chloride obtained above was added dropwise under ice-cooling. After 1 hour of stirring at room temperature, the solvent was evaporated under a reduced pressure, and the thus obtained residue was dissolved in ethyl acetate and washed with saturated sodium carbonate aqueous solution, 1N hydrochloric acid aqueous solution and saturated sodium chloride aqueous solution in that order. After drying on anhydrous magnesium sulfate and subsequent evaporation of the solvent under a reduced pressure, the resulting residue was applied to column chromatography, which was eluted with a mixed solvent of ethyl acetate and hexane (2:3, v/v) to obtain 283 mg of 4,4-difluoro-1-[4-(2-phenylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one. This product was recrystallized from ethyl acetate-hexane.

Workup

  1. customobtained
  2. additionabove was added dropwise under ice-
  3. temperaturecooling
  4. customthe solvent was evaporated under a reduced pressure
  5. dissolutionthe thus obtained residue was dissolved in ethyl acetate
  6. washwashed with saturated sodium carbonate aqueous solution, 1N hydrochloric acid aqueous solution and saturated sodium chloride aqueous solution in that order
  7. dry with materialAfter drying on anhydrous magnesium sulfate and subsequent evaporation of the solvent under a reduced pressure
  8. washwas eluted with a mixed solvent of ethyl acetate and hexane (2:3

Sources & evidence

ORD record
ord-5ac8d8c2056749febb899f3fe0b2f782
Source dataset
uspto-grants-1998_01
Patent number
US05710150

Reaction notes

Loading…