Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-Aminoazetidine, 3-BOC protected | HCID 1519405 | — |
| Reactant | 2,6-dichloro-N-(cyclohexylmethyl)-5-quinolinecarboxamide | HCID 86013022 | — |
| Catalyst | Tetrabutylammonium Bromide | HCID 74236 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | Ammonia | HCID 222 | 10% |
| Product | HCID 68808743 | HCID 68808743 | 32.3% |
Reaction Steps
3-Azetidinyl-carbamic acid, 1,1-dimethylethyl ester (0.5 g) was added to 2,6-dichloro-N-(cyclohexylmethyl)quinoline-5-carboxamide (Example 43(a)) (0.28 g), tetra-butylammonium bromide (0.28 g) and triethylamine (0.5 mL) in acetonitrile (4 mL). The reaction mixture was heated at 120° C. in a microwave for 1 hour, concentrated under reduced pressure and purified (SiO2, methanol:dichloromethane 4:96 as eluant). The residue (0.24 g) was dissolved in dichloromethane and trifluoroacetic acid (1 mL) added. The reaction mixture was stirred at room temperature for 1 hour, concentrated and then treated with 7M ammonia in methanol. Purification (Varian SCX cartridge using methanol and then 10% ammonia in methanol) gave the sub-titled compound as a solid (0.1 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07408065B2 |
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| Source dataset | uspto-grants-2008_08 |
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| ORD ID | ord-8ef91228a2204ca2b3a417b5af282208 |
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| Source note | uspto-grants-2008_08 |
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