2-Amino-5-methylbenzenesulfonic acid → 2-{7-[5-Chloro-4-(2-dimethylsulfamoyl-4-methyl-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

2-Amino-5-methyl-benzenesulfonic acid using 9-Fluorenylmethyl chloroformate was converted in an analogous manner to Example 820a, to 2-(9H-Fluoren-9-ylmethoxycarbonylamino)-5-methyl-benzenesulfonic acid, which was converted in an analogous manner to Example 820b, to (2-Chlorosulfonyl-4-methyl-phenyl)-carbamic acid 9H-fluoren-9-ylmethylester, which was converted in an analogous manner to Example 820c, to 2-Amino-5,N,N-trimethyl-benzenesulfonamide, which was converted, in an analogous procedure to Example 1d, to 2-(2,5-Dichloro-pyrimidin-4-ylamino)-5,N,N-trimethyl-benzenesulfonamide, 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. Product isolated as a tan foam (0.027 g, 27%). MP: 67-79° C. 1H NMR (400 MHz, CDCl3, δ, ppm): 9.13 (s, 1H), 8.32 (d, 1H, J=8.3 Hz), 8.11 (s, 1H), 7.98 (s, 1H), 7.69-7.67 (m, 1H), 7.48 (m, 1H), 7.39-7.34 (m, 1H), 6.64 (s, 1H), 3.86 (s, 3H), 3.30 (s, 2H), 3.14 (s, 3H), 2.98 (s, 3H), 2.91-2.86 (m, 2H), 2.76-2.64 (m, 12H), 2.41 (s, 3H). MS: 602.48 (MH)+.

Provenance & Evidence