HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → [5-Cyclopropyl-6-(4-fluoro-benzyl)-pyridin-2-yl]-(1,8-diaza-spiro[4.5]dec-1-yl)-methanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 1-[5-Cyclopropyl-6-(4-fluoro-benzyl)-pyridine-2-carbonyl]-1,8-diaza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester | HCID 90203564 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | [5-Cyclopropyl-6-(4-fluoro-benzyl)-pyridin-2-yl]-(1,8-diaza-spiro[4.5]dec-1-yl)-methanone | HCID 76281070 | 92.4% |
Reaction Steps
A solution of tert-butyl 1-(5-cyclopropyl-6-(4-fluorobenzyl)picolinoyl)-1,8-diazaspiro[4.5]decane-8-carboxylate (Example 111, 19 mg, 38.5 μmol) and 2,2,2-trifluoroacetic acid (43.9 mg, 29.5 μL, 385 μmol) in DCM (0.4 mL) was stirred for 12 h at ambient temperature. The reaction mixture was poured onto 20 mL saturated aqueous NaHCO3 solution/ice and extracted with EtOAc (2×20 mL). The combined extracts were washed with ice-water/brine (20 mL), dried over Na2SO4 and brought to dryness to give the title compound (14 mg, 92%) as colorless oil; MS (EI): m/e=394.5 [MH+].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09303012B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-35ee1ec2ca494a57a2d710ec0372f11d |
| Source note | uspto-grants-2016_04 |