Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Ammonium Acetate | HCID 517165 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | HCID 58368586 | HCID 58368586 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 58368535 | HCID 58368535 | — |
Reaction Steps
A mixture of 1-(5-chloro-8-{4-[(5-methylisoxazol-3-yl)carbonyl]piperazin-1-yl}quinolin-7-yl)ethanone (0.032 g, 0.080 mmol) and ammonium acetate (0.0618 g, 0.802 mmol) in methanol (0.3 mL) and acetonitrile (0.3 mL) was heated at 65° C. in a sealed tube for 1 hour. After cooling to room temperature, to the resulting mixture was added 1.0 M sodium cyanoborohydride in tetrahydrofuran (0.20 mL, 0.20 mmol). The reaction was heated at 65° C. overnight. The mixture was cooled to room temperature, quenched with sat. NaHCO3 solution, extracted with dichloromethane, dried over MgSO4 and concentrated to give the desired product. LCMS calculated for C20H23ClN5O2 (M+H)+: m/z=400.2; Found: 400.2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08680108B2 |
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| Source dataset | uspto-grants-2014_03 |
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| ORD ID | ord-27250e32154a461d8c691717b55ecc63 |
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| Source note | uspto-grants-2014_03 |
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