Hydrochloric Acid → HCID 86760946, compound

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([C:8](=[N:18]O)[C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[O:10])[CH:5]=[CH:4][N:3]=1.Cl>CO.[Pd]>[ClH:1].[NH2:18][CH:8]([C:6]1[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[CH:7]=1)[C:9]([C:11]1[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=1)=[O:10]

Participants

Procedure

With gentle heating, 22a (1.5 g; 5.4 mmol) was dissolved in methanol (15 ml). The solution was cooled to room temperature, HCl-containing methanol (20 ml) was added and the mixture was transferred into a two-necked flask. Pd—C 10% (150 mg) was introduced into the initial charge. The reaction vessel was evacuated using an oil pump, and H2 was then introduced via a gas inlet capillary (4×). At room temperature, the suspension was shaken in a closed three-necked flask under an atmosphere of H2 (240 strokes/min) until no more starting material could be detected by thin-layer chromatography (6 h). The suspension was filtered and the catalyst was washed with plenty of methanol. The combined filtrate was concentrated and the mustard-colored solid-amorphous residue was dried using an oil pump. The crude product was used without further purification for the next reaction step.