Hydrazine → HCID 9929207, compound

HRID 1635836Notes

Reaction equation

HRID 1635836 reaction equation
[NH2:1]N.C[N:4](C)[C:5]([CH3:31])=[CH:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]([N:17]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH2:21][N:20]3[CH:28]=[CH:29][CH:30]=[C:19]3[CH2:18]2)=[O:16])=[CH:11][CH:10]=1)=O>C(O)(=O)C>[CH3:31][C:5]1[NH:4][N:1]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([N:17]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[CH2:21][N:20]4[CH:28]=[CH:29][CH:30]=[C:19]4[CH2:18]3)=[O:16])=[CH:11][CH:10]=2)[CH:6]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 69844443HCID 69844443, compound

Product 1

HCID 9929207HCID 9929207, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Anhydrous hydrazine (0.10 g) was added to a solution of 3-Dimethylamino-1-[4-(5H,11H-pyrrolo[2,1-c][1,4]benzodiazepine-10-carbonyl)-phenyl]-2-buten-1-one (0.50 g) in glacial acetic acid (25 ml). The reaction mixture was refluxed for 18 hours and then concentrated under vacuum. The solid was extracted with dichloromethane and washed with saturated aqueous sodium bicarbonate solution. The dichloromethane solution was dried over anhydrous sodium sulfate and filtered through a short column of hydrous sodium magnesium silicate and further eluted with several volumes of dichloromethane. The combined organic phase was concentrated on a steam bath with the gradual addition of hexane to give an opaque solution. After cooling the amorphous solid was recovered by filtration to yield the product (0.33 g), MS, m/z: 368 (M)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 18 hours
  2. concentrationconcentrated under vacuum
  3. extractionThe solid was extracted with dichloromethane
  4. washwashed with saturated aqueous sodium bicarbonate solution
  5. dry with materialThe dichloromethane solution was dried over anhydrous sodium sulfate
  6. filtrationfiltered through a short column of hydrous sodium magnesium silicate
  7. washfurther eluted with several volumes of dichloromethane
  8. concentrationThe combined organic phase was concentrated on a steam bath with the gradual addition of hexane
  9. customto give an opaque solution
  10. temperatureAfter cooling the amorphous solid
  11. filtrationwas recovered by filtration

Sources & evidence

ORD record
ord-4e06950987b84607983ad077143c760b
Source dataset
uspto-grants-2003_01
Patent number
US06511974B1

Reaction notes

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