Hydrochloric Acid → HCID 178525986, compound

HRID 2368795Notes

Reaction equation

[F:1][C:2]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:3]=1[CH2:4][C:5]1[CH:6]=[C:7]([C:20](=[O:28])[CH:21]=[C:22]([OH:27])[C:23]([O:25]C)=[O:24])[C:8](=[O:19])[N:9]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[CH:10]=1.Cl>O1CCOCC1>[F:1][C:2]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:3]=1[CH2:4][C:5]1[CH:6]=[C:7]([C:20](=[O:28])[CH:21]=[C:22]([OH:27])[C:23]([OH:25])=[O:24])[C:8](=[O:19])[N:9]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[CH:10]=1

Participants

Conditions

Temperature: 95 °C

Procedure

To a stirred solution of methyl 4-(5-(2,4-difluorobenzyl)-1-(2-fluorobenzyl)-2-oxo-1,2-dihydropyridin-3-yl)-2-hydroxy-4-oxobut-2-enoate 7 (2.59 g, 5.7 mmol) in 1,4-dioxane (125 ml) was added 1N HCl (63 ml). The reaction mixture was allowed to stir at 95° C. for 2 h. The crude product was extracted with ethyl acetate (250 ml). The solvent was evaporated under reduced pressure. The solid was crystallized in chloroform and filtered under reduced pressure. Yield 1.61 g (64%). Yellow solid, mp 187-189° C., UV (MeOH) 394 nm (ε 14,917), 320 (ε 5671). 1H NMR (CDCl3-MeOH-d4, 500 MHz): δ 8.17 (d, 1H, J=3.4 Hz), 7.88 (s, 1H), 7.54 (s, 1H), 7.48-7.45 (m, 1H), 7.36-7.30 (m, 1H), 7.17-7.07 (m, 3H), 6.87-6.81 (m, 2H), 5.19 (s, 2H), 3.76 (s, 2H). 13C NMR (DMSO-d6, 125 MHz): δ 184.5, 173.3, 163.2, 161.7, 161.2, 159.8, 158.6, 144.6, 131.9, 130.0, 129.8, 124.5, 123.1, 123.0, 121.5, 116.8, 115.4, 111.6, 103.9, 100.8, 47.3, 29.2. HRMS [M+H]+ calculated mass 444.1059 for C23H17F3NO5. found 444.1042.

Workup

extractionThe crude product was extracted with ethyl acetate (250 ml)
customThe solvent was evaporated under reduced pressure
customThe solid was crystallized in chloroform
filtrationfiltered under reduced pressure

Sources & evidence

ORD record: ord-8839b7af13744a96acb7ce16e4a57a68
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703801B2

Reaction notes

Loading…