Diisopropylamine → {4-[1-(2-Chloro-4-fluoro-benzoyl)-1H-pyrazol-3-yl]-phenyl}-(5H,11H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl}methanone

HRID 2307337Notes

Reaction equation

HRID 2307337 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[NH:12]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([N:25]3[C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=4[CH2:29][N:28]4[CH:36]=[CH:37][CH:38]=[C:27]4[CH2:26]3)=[O:24])=[CH:19][CH:18]=2)=[N:13]1.C(NC(C)C)(C)C>ClCCl>[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([N:12]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([N:25]3[C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=4[CH2:29][N:28]4[CH:36]=[CH:37][CH:38]=[C:27]4[CH2:26]3)=[O:24])=[CH:19][CH:18]=2)=[N:13]1)=[O:5]

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 27365462-Chloro-4-fluorobenzoyl chlorideHCID 178519422HCID 178519422, compound

Product 1

HCID 9870998{4-[1-(2-Chloro-4-fluoro-benzoyl)-1H-pyrazol-3-yl]-phenyl}-(5H,11H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl}methanoneYield 73.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Portionwise, 2-chloro-4-fluorobenzoyl chloride (0.82 g) was added to a solution of [4-(1H-pyrazol-3-yl)-phenyl]-(5H,11H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-methanone (1.0 g) and diisopropylamine (0.55g) in dichloromethane (25 ml) which was cooled in an ice bath. The reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was washed with water and saturated sodium bicarbonate and dried over anhydrous sodium sulfate. The dichloromethane solution was passed through a short column of hydrous sodium magnesium silicate, eluting several additional volumes of dichloromethane. The eluent was evaporated to dryness to yield 1.06 g of the product as a solid, m.p. 150-157° C.; MS, m/z: 510 (M)+.

Workup

  1. temperaturewas cooled in an ice bath
  2. washThe reaction mixture was washed with water and saturated sodium bicarbonate
  3. dry with materialdried over anhydrous sodium sulfate
  4. washeluting several additional volumes of dichloromethane
  5. customThe eluent was evaporated to dryness

Sources & evidence

ORD record
ord-7c24b28984cc4e8bae5719b4bd20dabb
Source dataset
uspto-grants-2004_12
Patent number
US06831079B1

Reaction notes

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