Sodium hydride → HCID 9822464, compound

HRID 1635877Notes

Reaction equation

[H-].[Na+].[CH3:3][C:4]1[CH:8]=[CH:7][NH:6][N:5]=1.[H][H].[Cl:11][C:12]1[C:17]([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])=[CH:16][CH:15]=[C:14](Cl)[N:13]=1>CN(C)C=O.[Cl-].[Na+].O>[Cl:11][C:12]1[C:17]([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])=[CH:16][CH:15]=[C:14]([N:6]2[CH:7]=[CH:8][C:4]([CH3:3])=[N:5]2)[N:13]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a suspension of 60% sodium hydride in oil (0.1 g) in dimethylformamide (25 ml) was added dropwise 3-methylpyrazole (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 crude product was purified by preparative hplc (Dynamax c60 silica cartridge) eluting with 40% ethyl acetate in hexanes to give 0.21 g of colorless crystals, m.p. 171-172° C. MS, m/z: 404.2 (M+H)+, 807.1 (2M+H)+.

Workup

additionThe mixture was poured onto ice
extractionextracted with dichloromethane
dry with materialThe combined extracts were dried over anhydrous sodium sulfate
filtrationfiltered through a short column of anhydrous sodium magnesium silicate
customThe crude product was purified by preparative hplc (Dynamax c60 silica cartridge)
washeluting with 40% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-dd256c8e1918461c9e8850e5c6554906
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06511974B1

Reaction notes

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