Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | 1,1-Dichloroethane | HCID 6365 | — |
| Reactant | Cyano-borohydride | HCID 498716 | — |
| Reactant | 4-(3,5-Difluorophenyl)piperidine | HCID 16679312 | — |
| Reactant | 1-formyl-4-oxo-4H-quinolizine-3-carboxylic acid | HCID 77231453 | — |
| Product | HCID 44188037 | HCID 44188037 | — |
Reaction Steps
In a 2-5 mL Emrys™ process vial, a mixture of the 1-formyl-4-oxo-4H-quinolizine-3-carboxylic acid (35 mg, 0.16 mmol), 4-(3,5-difluorophenyl)piperidine (45.4 mg, 0.23 mmol), glacial acetic acid (0.055 mL, 0.97 mmol) and 0.80 mL of dichloroethane was stirred vigorously. To the stirring mixture was added resin-bound MP-cyanoborohydride (20.3 mg, 0.32 mmol). The mixture was heated via Emrys Optimizer™ microwave to 120° C. for 30 minutes. The reaction was filtered, providing material, which was purified by reverse phase HPLC to yield the title compound that gave a high resolution mass spectrum (ES+) m/z of 399.1512 calculated for M+H+ [C22H20F2N2O3: 399.1515].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08288409B2 |
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| Source dataset | uspto-grants-2012_10 |
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| ORD ID | ord-10d536a30c79443e925269f3bdda03b4 |
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| Source note | uspto-grants-2012_10 |
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