5-Chloro-2-phenoxyaniline → (5-Chloro-2-phenoxy-phenyl)-(7-ethyl-[1,8]naphthyridin-4-yl)-amine
Reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:6]([NH2:8])[CH:7]=1.Cl[C:17]1[CH:26]=[CH:25][N:24]=[C:23]2[C:18]=1[CH:19]=[CH:20][C:21]([CH2:27][CH3:28])=[N:22]2>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:6]([NH:8][C:17]2[C:18]3[C:23](=[N:22][C:21]([CH2:27][CH3:28])=[CH:20][CH:19]=3)[N:24]=[CH:25][CH:26]=2)[CH:7]=1Participants
3
Procedure
The product from Example 42b (100 mg, 0.46 mmol) was reacted with the product from Example 3f (88 mg, 0.46 mmol) following the procedure from Example 1g giving the title compound which was triturated with 2:1 ether/THF giving the product as a hydrochloride salt (134 mg, 70%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 1.34 (t, J=7.35 Hz, 3H) 3.02 (q, J=7.35 Hz, 2H) 6.69 (d, J=6.99 Hz, 1H) 6.97 (d, J=8.82 Hz, 2H) 7.10 (dd, J=7.35 Hz, 1H) 7.15 (d, J=8.82 Hz, 2H) 7.30 (dd, J=8.09 Hz, J=7.72 Hz, 2H) 7.56 (dd, J=2.94 Hz, J=9.19 Hz, 1H) 7.71 (d, J=2.57 Hz, 1H) 7.88 (d, J=8.82 Hz, 1H) 8.52 (d, J=6.99 Hz, 1H) 9.02 (d, J=8.45 Hz, 1H) 11.16 (br s, 1H) 14.56 (br s, 1H); MS (ESI+) m/z 376 (M−Cl)+; (ESI−) m/z 374 (M−HCl)−.