5-Chloro-2-methyl-1,8-naphthyridine → 2-(7-Methyl-[1,8]naphthyridin-4-ylamino)-biphenyl-4-carboxylic acid methyl ester
Reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:12])=[N:7]2.[CH3:13][O:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:19]([NH2:29])[CH:18]=1)=[O:16]>>[CH3:13][O:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[C:19]([NH:29][C:2]2[C:3]3[C:8](=[N:7][C:6]([CH3:12])=[CH:5][CH:4]=3)[N:9]=[CH:10][CH:11]=2)[CH:18]=1)=[O:16]Participants
3
Procedure
The product from Example 1d (0.0552 g, 0.309 mmol) was reacted with the product from Example 212c (0.070 g, 0.309 mmol) for 92 h following the procedure of Example 1g giving the crude title compound, which was purified by HPLC with AA. The resulting solid was triturated with 4N HCl in dioxane to generate the hydrochloride salt which was collected by vacuum filtration (0.0747 g, 55%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.72 (s, 3 H) 3.91 (s, 3 H) 6.27 (d, J=6.99 Hz, 1 H) 7.30 (m, J=6.99 Hz, 3 H) 7.52 (m, 2 H) 7.74 (d, J=8.82 Hz, 1 H) 7.79 (d, J=8.09 Hz, 1 H) 8.09 (d, J=1.47 Hz, 1 H) 8.16 (dd, J=7.91, 1.65 Hz, 1 H) 8.30 (d, J=6.99 Hz, 1 H) 9.15 (d, J=8.82 Hz, 1 H) 11.54 (s, 1 H); MS (ESI+) m/z 369.9 (M+H)+.
Sources & evidence
- ORD record
- ord-24bfcdb4f6e94fc5a023258b29e688f6
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07763731B2
Reaction notes
Loading…