CC1CN(C(=O)C(F)(F)F)CCC2N=C(O)C=CC1=2.O=P(Cl)(Cl)Cl.[Cl:25][C:26]1[CH:27]=[CH:28][C:29]2[CH:35]([CH3:36])[CH2:34][N:33](C(=O)C(F)(F)F)[CH2:32][CH2:31][C:30]=2[N:43]=1.C([O-])([O-])=O.[K+].[K+]>CO.CN(C=O)C>[Cl:25][C:26]1[CH:27]=[CH:28][C:29]2[CH:35]([CH3:36])[CH2:34][NH:33][CH2:32][CH2:31][C:30]=2[N:43]=1A mixture of 5-methyl-7-(trifluoroacetyl)-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepin-2-ol (100 mg, 365 μmol), DMF (50 μl) and POCl3 (5 ml) was heated at 100° C. for 3 h. The reaction mixture was concentrated in vacuo and purified by column chromatography rendering 101 mg (94%) of 2-chloro-5-methyl-7-(trifluoroacetyl)-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepine. MS (ESI) m/z 293.2/295.2. A mixture of 2-chloro-5-methyl-7-(trifluoroacetyl)-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepine (40.0 mg, 137 μmol), K2CO3 (80.0 mg) and MeOH (5 ml) was heated for 2 h at 70° C. The reaction mixture was concentrated in vacuo and purified by column chromatography furnishing 6.0 mg (22%) of 2-chloro-5-methyl-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepine. 1H-NMR (CDCl3) δ. 1H-NMR (CDCl3) δ 7.48 (d, 1H), 7.91 (d, 1H), 3.58 (s, 3H), 3.55-3.20 (m, 5H), 2.93 (dd, 1H), 2.73 (dd, 1H), 1.43 (d, 3H) ppm.
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