Sodium hydride → HCID 9889327, compound

HRID 2307326Notes

Reaction equation

HRID 2307326 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:8]=[CH:7][NH:6][N:5]=1.[H][H].Cl[C:12]1[N:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[C:15]([C:22]([N:24]2[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=3[CH2:28][N:27]3[CH:35]=[CH:36][CH:37]=[C:26]3[CH2:25]2)=[O:23])=[CH:14][N:13]=1>CN(C)C=O.CCCCCC>[CH3:3][C:4]1[CH:8]=[CH:7][N:6]([C:12]2[N:17]=[C:16]([C:18]([F:20])([F:19])[F:21])[C:15]([C:22]([N:24]3[C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=4[CH2:28][N:27]4[CH:35]=[CH:36][CH:37]=[C:26]4[CH2:25]3)=[O:23])=[CH:14][N:13]=2)[N:5]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 9865339HCID 9865339, compoundHCID 178418361HCID 178418361, compoundHCID 178428694HCID 178428694, compound

Product 1

HCID 9889327HCID 9889327, compoundYield 49.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Conditions

Temperature
110 °C

Procedure

To 60% sodium hydride in oil (0.15 g, degreased with hexane) in dimethylformamide (25 ml) was added 3-methylpyrazole (0.25 g). When the hydrogen evolution subsided, (2-chloro-4-trifluoromethyl-pyrimidin-5-yl)-(5H,11H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-methanone (0.98 g) was added. The reaction mixture was heated for 18 hours in a sand bath (internal temperature 110° C.). The mixture was then poured onto ice and further diluted with a saturated saline solution. The precipitate was filtered, redissolved in dichloromethane and dried over anhydrous sodium sulfate. Purification was aided by filtration through a short column of hydrous sodium magnesium silicate and further elution with several volumes of dichloromethane. The combined eluate was concentrated on a hot plate with the gradual addition of hexane until crystallization occurred. After cooling, the solid was collected by filtration to yield the title compound (0.54 g) as colorless crystals, m.p. 202-204° C.

Workup

  1. additionThe mixture was then poured onto ice
  2. additionfurther diluted with a saturated saline solution
  3. filtrationThe precipitate was filtered
  4. dissolutionredissolved in dichloromethane
  5. dry with materialdried over anhydrous sodium sulfate
  6. customPurification
  7. filtrationwas aided by filtration through a short column of hydrous sodium magnesium silicate and further elution with several volumes of dichloromethane
  8. concentrationThe combined eluate was concentrated on a hot plate with the gradual addition of hexane until crystallization
  9. temperatureAfter cooling
  10. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-a7e6591e5f024ddabefbfab08a7354e5
Source dataset
uspto-grants-2004_12
Patent number
US06831079B1

Reaction notes

Loading…