Cl[C:2]1[CH:31]=[N:30][C:5]2[S:6](=[O:29])(=[O:28])[CH2:7][CH2:8][N:9]([C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][C:18]=4[F:20])[N:13]=[C:12]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=4)[C:11]=3[CH3:27])[C:4]=2[CH:3]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[NH:66]1[CH2:71][CH2:70][O:69][CH2:68][CH2:67]1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:20][C:18]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:19]=1[C:10]([N:9]1[CH2:8][CH2:7][S:6](=[O:29])(=[O:28])[C:5]3[N:30]=[CH:31][C:2]([N:66]4[CH2:71][CH2:70][O:69][CH2:68][CH2:67]4)=[CH:3][C:4]1=3)=[C:11]([CH3:27])[C:12]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1)=[N:13]2Prepared according to procedure N by heating a solution of 7-chloro-1-(5-fluoro-3-methyl-2-pyridin-2-ylquinolin-4-yl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]thiazine 4,4-dioxide (34 mg, 0.075 mmol), Pd2dba3 (6.8 mg, 7.5 μmol), XPhos (7.13 mg, 0.015 mmol), morpholine (6.51 μL, 0.075 mmol) and sodium tert-butoxide (14.4 mg, 0.149 mmol) in toluene (2.0 mL) in the microwave for 2 h at 110° C. After this time the reaction was cooled to rt and partitioned between EtOAc (60 mL) and NaHCO3 (20 mL, saturated aqueous solution). The separated organic layer was dried over MgSO4, filtered and evaporated in vacuo. Purification by reverse phase HPLC (10 to 60% acetonitrile in water) gave 1-(5-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-7-(4-morpholinyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]-thiazine 4,4-dioxide. 1H NMR (400 MHz, chloroform-d) δ ppm 8.75 (1H, dt, J=4.8, 1.5 Hz), 8.05-8.12 (1H, m), 7.94 (2H, dt, J=4.6, 0.9 Hz), 7.87 (1H, d, J=2.3 Hz), 7.70 (1H, td, J=8.2, 5.4 Hz), 7.44 (1H, q, J=4.8 Hz), 7.23-7.30 (1H, m), 5.62 (1H, d, J=2.3 Hz), 4.17-4.32 (2H, m), 3.64-3.76 (5H, m), 3.49-3.60 (1H, m), 2.87-3.04 (4H, m), 2.46 (3H, s). Mass Spectrum (ESI) m/e=506.0 (M+1).
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