Sodium hydride → HCID 10137963, compound

HRID 1635880Notes

Reaction equation

HRID 1635880 reaction equation
[H-].[Na+].[CH3:3][C:4]1[N:8]=[CH:7][NH:6][N:5]=1.[H][H].F[C:12]1[CH:17]=[CH:16][C:15]([C:18]([N:20]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[CH2:24][N:23]3[CH:31]=[CH:32][CH:33]=[C:22]3[CH2:21]2)=[O:19])=[C:14]([C:34]([F:37])([F:36])[F:35])[CH:13]=1>CN(C)C=O.[Cl-].[Na+].O>[CH3:3][C:4]1[N:8]=[CH:7][N:6]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([N:20]3[C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=4[CH2:24][N:23]4[CH:31]=[CH:32][CH:33]=[C:22]4[CH2:21]3)=[O:19])=[C:14]([C:34]([F:35])([F:36])[F:37])[CH:13]=2)[N:5]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 9799697HCID 9799697, compoundHCID 178418361HCID 178418361, compoundHCID 178433329HCID 178433329, compound

Product 1

HCID 10137963HCID 10137963, compoundYield 39.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
110 °C

Procedure

To a suspension of 60% sodium hydride in oil (0.3 g) in dimethylformamide (50 ml) was added dropwise 3-methyl-1,2,4-triazole (0.45 g). After hydrogen gas evolution ceased, 4-fluoro-2-trifluoromethyl-phenyl-(5H,11H-pyrrolo[2,1-c][1,4]-benzodiazepine-10-yl)-methanone (1.76 g) was added and the reaction mixture was heated in a sand bath at 110° C. for 18 hours. The mixture was poured onto ice, diluted with brine, and extracted with dichloromethane. The combined extracts were dried over anhydrous sodium sulfate and filtered through a short column of anhydrous sodium magnesium silicate. The solution was concentrated in vacuo and the residue was triturated with diethyl ether to give 0.81 g of the title compound as colorless crystals, m.p. 148-150° C., MS m/z: 438.2 (M+H)+, 875.8 (2M+H)+.

Workup

  1. additionThe mixture was poured onto ice
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  4. filtrationfiltered through a short column of anhydrous sodium magnesium silicate
  5. concentrationThe solution was concentrated in vacuo
  6. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-f8852fcdffa845289fb5ec510f2a6b93
Source dataset
uspto-grants-2003_01
Patent number
US06511974B1

Reaction notes

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