Water → HCID 178418377, compound

HRID 342312Notes

Reaction equation

HRID 342312 reaction equation
[Br-].[Br-].[Br-].[C:4]1([N+:10](C)(C)C)[CH:9]=CC=CC=1.[C:14]1([N+](C)(C)C)[CH:19]=CC=C[CH:15]=1.C1([N+:30](C)(C)C)C=CC=CC=1.O1CCCC1.O=[C:40]1[C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=2[N:44]([C:51]([C:53]2[CH:70]=[CH:69][C:56]([NH:57][C:58](=[O:68])[C:59]3[CH:64]=[CH:63][CH:62]=[CH:61][C:60]=3C(C)C)=[CH:55][CH:54]=2)=[O:52])[CH2:43][CH2:42][CH2:41]1.[OH2:71]>>[CH:14]([O:71][C:64]1[CH:63]=[CH:62][CH:61]=[CH:60][C:59]=1[C:58]([NH:57][C:56]1[CH:55]=[CH:54][C:53]([C:51]([N:44]2[C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=3[C:40]3[NH:30][C:4]([CH3:9])=[N:10][C:41]=3[CH2:42][CH2:43]2)=[O:52])=[CH:70][CH:69]=1)=[O:68])([CH3:19])[CH3:15]

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 107885654'-[(5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)carbonyl)-2-isopropylbenzanilideHCID 17977687Phenyltrimethylammonium bromide dibromide

Product 1

HCID 178418377HCID 178418377, compound

Procedure

With cooling on an ice bath, a 793 mg portion of phenyltrimethylammonium tribromide was added to 20 ml of tetrahydrofuran solution containing 1.0 g of 4'-[(5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)carbonyl)-2-isopropylbenzanilide, and the mixture was warmed up to room temperature. Filtration was carried out when disappearance of the color of bromine was confirmed after about 60 minutes. The filtered material was washed with tetrahydrofuran, and the filtrates were combined and concentrated. The thus obtained residue was dissolved in chloroform, washed with a sodium bicarbonate aqueous solution and then dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was further evaporated to dryness using a vacuum pump. The thus obtained solid substance was dissolved in 40 ml of chloroform, and the resulting solution was mixed with 1.11 g of acetamidine hydrochloride and 2.26 g of potassium carbonate and subjected to 20 hours of heating under reflux in a stream of argon. The resulting reaction solution was mixed with water to effect phase separation, and the organic layer was separated and dried over anhydrous magnesium sulfate. After removing the solvent by distillation under a reduced pressure, the thus obtained residue was crystallized from toluene to obtain 640 mg of 2-isopropoxy-4'-[(2-methyl-1,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepin-6-yl)carbonyl]benzanilide. A 563 mg portion of this compound was dissolved in 5.5 ml of ethyl alcohol, mixed with 0.45 ml of 4N hydrochloric acid-ethyl acetate and recrystallized to obtain 400 mg of 2-isopropyl-4'-[(2-methyl-1,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepin-6-yl)carbonyl)benzanilide hydrochloride.

Workup

  1. temperatureWith cooling on an ice bath
  2. filtrationFiltration
  3. washThe filtered material was washed with tetrahydrofuran
  4. concentrationconcentrated
  5. dissolutionThe thus obtained residue was dissolved in chloroform
  6. washwashed with a sodium bicarbonate aqueous solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationAfter distilling off the solvent
  9. customthe residue was further evaporated to dryness
  10. dissolutionThe thus obtained solid substance was dissolved in 40 ml of chloroform
  11. additionthe resulting solution was mixed with 1.11 g of acetamidine hydrochloride and 2.26 g of potassium carbonate
  12. waitsubjected to 20 hours
  13. temperatureof heating
  14. temperatureunder reflux in a stream of argon
  15. customThe resulting reaction solution
  16. customphase separation
  17. customthe organic layer was separated
  18. dry with materialdried over anhydrous magnesium sulfate
  19. customAfter removing the solvent
  20. distillationby distillation under a reduced pressure
  21. customthe thus obtained residue was crystallized from toluene

Sources & evidence

ORD record
ord-2786d3c8276b49188e071fa1ad695156
Source dataset
uspto-grants-1999_01
Patent number
US05856564

Reaction notes

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