2-Chloro-6-morpholin-4-yl-pyrimidine-4-carboxylic acid[4-(2-morpholin-4-yl-ethoxy)-naphthalen-1-yl]-amide → HCID 59553189, compound

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To a mixture of 2-chloro-6-morpholin-4-yl-pyrimidine-4-carboxylic acid[4-(2-morpholin-4-yl-ethoxy)-naphthalen-1-yl]-amide (95 mg) and 10% Pd/C (10 mg) in ethyl acetate (4 ml) is added a few drops of triethylamine. The mixture is then shaken at room temperature under hydrogen at 50 psi for 8 h. The solvent is then removed under reduced pressure and the residue purified by column chromatography on silica gel eluted with ethyl acetate: hexane (1:1) to 100% ethyl acetate to provide 6-morpholin-4-yl-pyrimidine-4-carboxylic acid[4-(2-morpholin-4-yl-ethoxy)-naphthalen-1-yl]-amide as a solid (22 mg). Mp: 50-51° C. 1H NMR (300 MHz, DMSO-d6) δ 10.62 (s, 1H), 8.70 (s, 1H), 8.22 (d, J=7.2 Hz, 1H), 7.83 (d, J=8.1 Hz, 1H), 7.66 (d, J=8.1 Hz, 1H), 7.57 (m, 2H), 7.42 (s, 1H), 7.04 (d, J=8.1 Hz, 1H), 4.30 (t, J=5.7, 2H), 3.70 (m, 10H), 3.60 (t, J=4.5 Hz, 2H) 2.87 (t, J=5.7 Hz, 2H), 2.56 (brm, 4H). MS: 463 (M+1).

Provenance & Evidence