Morpholine → 2-{7-[5-Chloro-4-(2-methyl-4-morpholin-4-yl-phenylamino)-pyrimidin-2-ylamino]-8-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl}-N,N-dimethyl-acetamide

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Reaction Steps

4-Fluoro-2-methyl-1-nitro-benzene using Morpholine was converted in an analogous manner to Example 171b, to 4-(3-Methyl-4-nitro-phenyl)-morpholine which was converted in an analogous manner to Example 31f, to 2-Methyl-4-morpholin-4-yl-phenylamine, which was converted in an analogous manner to Example 1d, to (2,5-Dichloro-pyrimidin-4-yl)-(2-methyl-4-morpholin-4-yl-phenyl)-amine which was converted to the title compound in an analogous manner to Example 61e using 2-(7-Amino-8-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-N,N-dimethyl-acetamide (54.0 mg, 0.000194 mol). Product isolated as an off-white solid (0.040 g, 39%). MP: 223-226° C. 1H NMR (400 MHz, CDCl3, δ, ppm): 8.00 (d, 1H, J=1.0 Hz), 7.86 (s, 1H), 7.52-7.45 (m, 2H), 6.83-6.76 (m, 2H), 6.68 (s, 1H), 6.57 (s, 1H), 3.91-3.86 (m, 4H), 3.82 (s, 3H), 3.25 (s, 2H), 3.20-3.13 (m, 7H), 2.99 (s, 3H), 2.85-2.80 (m, 2H), 2.67-2.56 (m, 6H), 2.26 (s, 3H). MS: 580.29 (MH)+.

Provenance & Evidence