Dichloromethane → phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone O-(3-aminopropyl)oxime hydrochloride
Reaction equation
[C:1]1([C:7](=[N:17][O:18][CH2:19][CH2:20][CH2:21][NH:22]C(=O)OC(C)(C)C)[C:8]2[NH:16][C:11]3=[CH:12][N:13]=[CH:14][CH:15]=[C:10]3[CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O.C(Cl)[Cl:38]>>[ClH:38].[NH2:22][CH2:21][CH2:20][CH2:19][O:18][N:17]=[C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]1[NH:16][C:11]2=[CH:12][N:13]=[CH:14][CH:15]=[C:10]2[CH:9]=1Participants
4
Procedure
tert-Butyl 3-[[[phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methylene]amino]oxy]propylcarbamate (Example 76) (60 mg, 0.15 mmol) was dissolved in methylene chloride (4 mL) and trifluoroacetic acid (1 mL) was added. The reaction mixture was stirred for 1 h. The solvents were removed under vacuum and the residue was dissolved in ethyl acetate. Saturated sodium bicarbonate solution was added and the mixture was stirred for 10 min. The layers were separated and the aqueous layer extracted with ethyl acetate (2×). The combined organic extracts were washed with water and brine, dried over sodium sulfate, and concentrated to an oil. The oil was dissolved in ethyl acetate (4 mL), 2 M ethereal hydrogen chloride (0.2 mL) was added and the precipitate formed. Removal of the solvents and drying under vacuum produced phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone O-(3-aminopropyl)oxime hydrochloride, a mixture of isomers (39 mg, 71%) as an off-white solid: mp 168-174° C. dec.; 1H NMR (500 MHz, CD3OD) δ2.02-2.31 (2H, m), 2.98-3.27 (2H, m), 4.47-4.59 (2H, m), 6.75 (0.24H, s) 7.12 (0.76H, s), 7.47-7.59 (5H, m), 8.05-8.27 (2H, m), 8.96 (0.24H, s), 9.13 (0.76H, br s); ESI MS m/z 295 [C17H18N4O+H]+; HPLC (Method A) 91.5% (AUC), tR=14.0 min.