Ethanol → HCID 67282625, 화합물

In a 500-mL reaction vessel was placed methanesulfonic acid 1-(5-benzyloxy-1-methyl-4-oxo-1,4-dihydro-pyridin-2-yl)-2,2,2-trifluoro-ethyl ester (1.80 g, 4.60 mmol), and ethanol (120 mL). The mixture was sonicated to give a clear solution. To the solution was added 1.80 g of Pd/C (10 wt. %, dry basis, on activated carbon, wet, Degussa type E101 NE/W). Hydrogenation was carried out under a hydrogen atmosphere set at a pressure of 50 psi. The reaction was completed within 90 min. The reaction mixture was diluted with methanol (120 mL), and the resulting mixture was sonicated for 10 min. The reaction mixture was then filtered through a short hydrochloric acid pre-treated CELITE™ bed. The filtrate was collected, and concentrated in vacuo to a volume of about 100 mL. To the resulting solution was added morpholine polymer-bound beads (1% cross-linked w/DVB, 200-400 mesh, 2.5-4.0 mmol N/g, 5.2 g), and the mixture was vortexed for 3 h. The morpholine beads were removed by filtration. Upon partial concentration in vacuo, a solid separated and the first crop of the title compound was obtained as the free base (0.74 g, 77% yield, HPLC Method 1 (Example 24); RT=8.2 min, HPLC purity (peak percent area): 98.7% at λ=280 nm). 1H NMR (CD3OD) δ ppm: 7.55 (s, 1H), 6.52 (s, 1H), 3.77 (q, J=10 Hz, 2H), 3.78 (s, 3H); MS-ESI (m/z): 208.2 ([M+1]+, 100%), 188.2, 139.2.

1. customIn a 500-mL reaction vessel
2. customThe mixture was sonicated
3. customto give a clear solution
4. customthe resulting mixture was sonicated for 10 min
5. filtrationThe reaction mixture was then filtered through a short hydrochloric acid pre-treated CELITE™ bed
6. customThe filtrate was collected
7. concentrationconcentrated in vacuo to a volume of about 100 mL
8. additionTo the resulting solution was added morpholine polymer-bound beads (1% cross-linked w/DVB, 200-400 mesh, 2.5-4.0 mmol N/g, 5.2 g)
9. waitthe mixture was vortexed for 3 h
10. customThe morpholine beads were removed by filtration
11. concentrationUpon partial concentration in vacuo
12. customa solid separated

ORD 기록

ord-a74e67a0e75247bda7e1328fc62f2258

출처 데이터셋

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08673943B2