Sodium hydride → HCID 9844131, compound

HRID 1635879Notes

Reaction equation

HRID 1635879 reaction equation
[H-].[Na+].[CH3:3][C:4]1[N:8]=[CH:7][NH:6][N:5]=1.[H][H].[Cl:11][C:12]1[CH:17]=[C:16](F)[CH:15]=[CH:14][C:13]=1[C:19]([N:21]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[CH2:25][N:24]2[CH:32]=[CH:33][CH:34]=[C:23]2[CH2:22]1)=[O:20]>CN(C)C=O.[Cl-].[Na+].O>[Cl:11][C:12]1[CH:17]=[C:16]([N:6]2[CH:7]=[N:8][C:4]([CH3:3])=[N:5]2)[CH:15]=[CH:14][C:13]=1[C:19]([N:21]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[CH2:25][N:24]2[CH:32]=[CH:33][CH:34]=[C:23]2[CH2:22]1)=[O:20]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 9798048HCID 9798048, compoundHCID 178418361HCID 178418361, compoundHCID 178433329HCID 178433329, compound

Product 1

HCID 9844131HCID 9844131, compoundYield 62%

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, 2-chloro-4-fluorophenyl-(5H,11H-pyrrolo[2,1-c][1,4]benzodiazepine-10-yl)-methanone (1.70 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 1.25 g of the title compound as colorless crystals, m.p. 191-193° C., MS m/z: 404.1 (M+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-7b008f1896224ad2a472724834dd9d80
Source dataset
uspto-grants-2003_01
Patent number
US06511974B1

Reaction notes

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