Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methyl isonipecotate | HCID 424914 | — |
| Reactant | 2-Chloro-6-methoxyquinazoline | HCID 59254852 | — |
| Solvent | Isopropanol | HCID 3776 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 67975007 | HCID 67975007 | 101.4% |
Reaction Steps
A mixture of 2-chloro-6-methoxyquinazoline (Intermediate 8, 700 mg, 3.60 mmol), methyl 4-piperidinecarboxylate (2.58 g, 18.0 mmol) and Et3N (729 mg, 7.20 mmol) in iPrOH (15 mL) was heated to 50° C. for 16 hours. The reaction mixture was diluted with EtOAc (100 mL) and washed with H2O (30 mL×2) and brine (30 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by prep-HPLC (0.1% TFA as additive). Most of CH3CN was removed under reduced pressure and the remaining solvent was removed by lyophilization to give the product (1.10 g, yield: 73%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09364481B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-7c670a8513c7443bb82ed8d748a8b848 |
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| Source note | uspto-grants-2016_06 |
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