Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 2-Methoxyethanol | HCID 8019 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | N-[2-(3-Cyano-1H-indol-5-yl)-ethyl]-4-[2-chloropyrimidin-4-yl]benzamide | HCID 18617562 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 18617857 | HCID 18617857 | — |
Reaction Steps
To a solution of 2-methoxyethanol (0.118 mL, 1.50 mmoles) in DMSO (5 mL) was added sodium hydride (Aldrich, 60% dispersion, 0.0720 g, 1.80 mmoles), followed by stirring until H2 evolution ceased (15 minutes). One milliliter of this alkoxide stock solution was added to N-[2-(3-Cyano-1H-indol-5-yl)-ethyl]-4-[2-chloropyrimidin-4-yl]benzamide (0.147 g, 0.249 mmoles, reference example 1az), followed by heating (60° C.). After two hours, another 0.5 mL of the alkoxide stock solution was added. After two more hours, the reaction was quenched with water (40 mL) and the resulting precipitate collected by filtration. The precipitate was washed with water and CH2Cl2 and dried under vacuum to give the product as a white solid. MS (ion spray) m/z 442 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06541505B1 |
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| Source dataset | uspto-grants-2003_04 |
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| ORD ID | ord-4385da7a1dae4331a2cfb2a4db7227cf |
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| Source note | uspto-grants-2003_04 |
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