Water → HCID 10135367, compound

HRID 1635826Notes

Reaction equation

HRID 1635826 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[CH:10][C:9]([C:12]([N:14]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[CH2:18][N:17]4[CH:25]=[CH:26][CH:27]=[C:16]4[CH2:15]3)=[O:13])=[CH:8][CH:7]=2)=[N:2]1.[C:28](OC(=O)C)(=[O:30])[CH3:29].O>N1C=CC=CC=1>[CH:27]1[CH:26]=[CH:25][N:17]2[CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N:14]([C:12]([C:9]3[CH:10]=[CH:11][C:6]([C:3]4[CH:4]=[CH:5][N:1]([C:28](=[O:30])[CH3:29])[N:2]=4)=[CH:7][CH:8]=3)=[O:13])[CH2:15][C:16]=12

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 178519422HCID 178519422, compound

Product 1

HCID 10135367HCID 10135367, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of [4-(1H-pyrazol-3-yl)-phenyl]-(5H,11H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-methanone (0.50 g) in dry pyridine (10 ml) was added acetic anhydride (0.20 g). After stirring at room temperature for 18 hours the reaction mixture was poured into water and the precipitate was collected by filtration. The crude product was dissolved in dichloromethane and dried over anhydrous sodium sulfate. This solution was filtered through a short column of hydrous sodium magnesium silicate, eluting with several additional volumes of dichloromethane. The eluant was concentrated on a hot plate with the gradual addition of hexane until crystallization occurred. After cooling, the crystals were collected by filtration to yield the title compound (0.46 g), m.p. 192-194° C.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. dissolutionThe crude product was dissolved in dichloromethane
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThis solution was filtered through a short column of hydrous sodium magnesium silicate
  5. washeluting with several additional volumes of dichloromethane
  6. concentrationThe eluant was concentrated on a hot plate with the gradual addition of hexane until crystallization
  7. temperatureAfter cooling
  8. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-f770b81f388f495bba75d9ee2042b7d3
Source dataset
uspto-grants-2003_01
Patent number
US06511974B1

Reaction notes

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