Dimethylamine → HCID 67305329, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-chloro-N-(7-methoxy-3-(2-(methylamino)pyrimidin-4-yl)naphthalen-1-yl)acetamide 34 (0.125 mg, 0.35 mmol) in N,N-dimethylacetamide (1 mL), dimethylamine (1.5 mL, 2M solution in methanol, 3 mmol) was added. The reaction mixture was stirred at 60° C. overnight. The crude reaction mixture was concentrated under high vacuum and which was purified by reverse phase chromatography on preparative LC/UV/MS system using a mass triggered fractionation. Compound was eluted from the HPLC column (Maccel 120-10-C18 SH 10 μm 20 mmID×50 mm) at 88 mL/min with acetonitrile/water gradient using 0.1% FA as a modifier. 2-(dimethylamino)-N-(7-methoxy-3-(2-(methylamino)pyrimidin-4-yl)naphthalen-1-yl)acetamide 137 was isolated as a yellow-orange solid (0.050 g). M.p.=70-73° C. 400 MHz 1H NMR (DMSO-d6) δ: 9.96 (s, 1H), 8.49 (s, 1H), 8.38 (s, 2H), 8.01 (d, J=8.6 Hz, 1H), 7.29-7.14 (m, 4H), 3.92 (s, 3H), 3.24 (s, 2H), 2.90 (br s, 3H), 2.42 (s, 6H); Experimental Elemental Analysis (0.13 equivalents of water)=65.32% C, 6.36% H, 18.75% N; Calculated Elemental Analysis 65.32% C, 6.37% H, 19.04% N; LCMS (m/z): 367 [M+H].

Provenance & Evidence