Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Ammonium Acetate | HCID 517165 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | HCID 58368581 | HCID 58368581 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 58368421 | HCID 58368421 | — |
Reaction Steps
A mixture of 1-[5-chloro-8-(4-cyclohexylpiperazin-1-yl)quinolin-7-yl]ethanone (0.094 g, 0.25 mmol) and ammonium acetate (0.195 g, 2.53 mmol) in methanol (1 mL) and acetonitrile (1 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 (0.632 mL, 0.632 mmol). The reaction was heated at 65° C. overnight. The mixture was cooled to room temperature, quenched with sat. NaHCO3 solution and extracted with dichloromethane. The combined organic layers were dried over MgSO4 and concentrated to give the desired product. LCMS calculated for C21H30ClN4 (M+H)+: m/z=373.2; Found: 373.3.
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-f6096d57bf50425986e394938960116f |
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| Source note | uspto-grants-2014_03 |
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