HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → [6-(3-Chloro-4-hydroxy-5-methoxyphenyl)-4-(2,8-diazaspiro[4,5]decan-8-yl)quinolin-3-yl](cyclopropyl)methanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | tert-Butyl 8-[6-(3-chloro-4-hydroxy-5-methoxyphenyl)-3-(cyclopropanecarbonyl)quinolin-4-yl]-2,8-diazaspiro[4,5]decane-2-carboxylate | HCID 68091922 | — |
| Product | [6-(3-Chloro-4-hydroxy-5-methoxyphenyl)-4-(2,8-diazaspiro[4,5]decan-8-yl)quinolin-3-yl](cyclopropyl)methanone | HCID 66715553 | 38% |
Reaction Steps
Following general procedure A-2, tert-butyl 8-[6-(3-chloro-4-hydroxy-5-methoxyphenyl)-3-(cyclopropanecarbonyl)quinolin-4-yl]-2,8-diazaspiro[4,5]decane-2-carboxylate (110 mg, 0.097 mmol) was reacted with TFA (2 mL) to afford the desired product (18 mg, 38%) as a green solid: 1H NMR (300 MHz, CD3OD) δ 8.79 (s, 1H), 8.29 (s, 1H), 8.02 (s, 2H), 7.30 (d, J=2.1 Hz, 1H), 7.23 (d, J=2.1 Hz, 1H), 3.98 (s, 4H), 3.08 (s, 2H), 2.65-2.52 (m, 1H), 2.03-1.81 (m, 7H), 1.37-1.16 (m, 8H); ESI MS m/z 492 [C28H30ClN3O3+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09120749B2 |
| Source dataset | uspto-grants-2015_09 |
| ORD ID | ord-83c6ad2ef62a4a588f5728686a7cfbba |
| Source note | uspto-grants-2015_09 |