Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyrazole | HCID 1048 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 9841710 | HCID 9841710 | — |
| Reactant | HCID 178418361 | HCID 178418361 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | HCID 9821737 | HCID 9821737 | 24.7% |
Reaction Steps
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)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06511974B1 |
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| Source dataset | uspto-grants-2003_01 |
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| ORD ID | ord-a29aa51fe5694b809841612e5ae2f8ea |
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| Source note | uspto-grants-2003_01 |
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