Pyrazole → HCID 9821737, compound

HRID 1635876Notes

Reaction equation

HRID 1635876 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[N:4]1.[H][H].[Cl:10][C:11]1[C:16]([C:17]([N:19]2[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[CH2:23][N:22]3[CH:30]=[CH:31][CH:32]=[C:21]3[CH2:20]2)=[O:18])=[CH:15][CH:14]=[C:13](Cl)[N:12]=1>CN(C)C=O.[Cl-].[Na+].O>[Cl:10][C:11]1[C:16]([C:17]([N:19]2[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[CH2:23][N:22]3[CH:30]=[CH:31][CH:32]=[C:21]3[CH2:20]2)=[O:18])=[CH:15][CH:14]=[C:13]([N:3]2[CH:7]=[CH:6][CH:5]=[N:4]2)[N:12]=1

Participants

7

Reactant 4

HCID 1048PyrazoleHCID 24758Sodium hydrideHCID 9841710HCID 9841710, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9821737HCID 9821737, compoundYield 24.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
110 °C

Procedure

To a suspension of 60% sodium hydride in oil (0.1 g) in dimethylformamide (25 ml) was added dropwise pyrazole (0.15 g). After hydrogen gas evolution ceased, (2,6-dichloropyridin-3-yl)(5H,11H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-methanone (0.67 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 triturated with diethyl ether to give 0.18 g of the title compound as a colorless solid, m.p. 133-135° C. MS m/z: 390.8 (M+H)+, 779.1 (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. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-a29aa51fe5694b809841612e5ae2f8ea
Source dataset
uspto-grants-2003_01
Patent number
US06511974B1

Reaction notes

Loading…