Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 58044825 | HCID 58044825 | — |
| Reactant | (S)-2-(Hydroxymethyl)-6,8-dihydrospiro[cyclopenta[g]quinoline-7,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one | HCID 67016575 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 46916821 | HCID 46916821 | — |
Reaction Steps
To a solution of (±)-3,3-dimethyl-5-phenylpyrrolidin-2-one (221 mg, 0.893 mmol, described in Intermediate 51) in DMF (0.5 mL), at ambient temperature, was added sodium hydride (60% dispersion in mineral oil; 37 mg, 0.923 mmol). The resulting mixture was stirred for 30 min, then (S)-2-(chloromethyl)-6,8-dihydrospiro[cyclopenta[g]quinoline-7,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (100 mg, 0.298 mmol, described in Intermediate 7) was added and the resulting mixture was stirred at ambient temperature for 2 h. The reaction mixture was quenched with H2O (0.1 mL) and purified directly by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH—100:0 to 95:5, to give the title compound. MS: m/z=547 (M+1). HRMS: m/z=547.2466; calculated m/z=547.2452 for C32H31N6O3.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08778957B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-0e80a5ed302c4796b6c7c0478179ee3e |
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| Source note | uspto-grants-2014_07 |
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