Ammonia → 1-(3-Aminomethyl-2-fluorobenzyl)-3-bromo-4-(2,4-difluorobenzyloxy)-1H-pyridin-2-one

HRID 1831931

Reaktionsgleichung

[Br:1][C:2]1[C:3](=[O:28])[N:4]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25]Br)[C:20]=2[F:27])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17].[NH3:29]>CO>[NH2:29][CH2:25][C:21]1[C:20]([F:27])=[C:19]([CH:24]=[CH:23][CH:22]=1)[CH2:18][N:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2[F:17])=[C:2]([Br:1])[C:3]1=[O:28]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A sealed tube containing a solution of 3-bromo-1-(3-bromomethyl-2-fluorobenzyl)-4-(2,4-difluorobenzyloxy)-1H-pyridin-2-one (0.24 g, 0.45 mmol) and NH3 (24 mL of a 7 N solution in MeOH, 168 mmol) was heated at 80° C. for 1 h. The reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Purification by flash column chromatography (silica, eluent 99.5:0.5 to 96:4 methylene chloride/methanol) afforded a white solid (0.12 g, 60%): mp 160-163° C.; 1H NMR (300 MHz, CDCl3) δ 7.46-7.45 (m, 1H), 7.44-7.35 (m, 2H), 7.34-7.26 (m, 1H), 7.15-7.05 (m, 1H), 6.95-6.80 (m, 2H), 6.11 (d, J=9 Hz, 1H), 5.21 (s, 2H), 5.19 (s, 2H), 3.90 (s, 2H). ES HRMS m/z 453.0442 (M+H C20H17BrF3N2O2 requires 453.0420).

Aufarbeitung

temperatureThe reaction mixture was cooled to room temperature
customthe solvent was removed under reduced pressure
customPurification by flash column chromatography (silica, eluent 99.5:0.5 to 96:4 methylene chloride/methanol)

Quellen und Nachweise

ORD-Eintrag: ord-5242c2c904764ad2b5435839c0d3aaa0
Quelldatensatz: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07067540B2

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