5-Fluoro-6-methoxypyridin-3-amine → 5-(4-Amino-6-methyl-1,3,5-triazin-2-YL)-N-(5-fluoro-6-methoxypyridin-3-YL)-2,3'-bipyridin-6-amine
Reaction equation
F[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:5]=[CH:4][C:3]=1[C:14]1[N:19]=[C:18]([CH3:20])[N:17]=[C:16]([N:21](CC2C=CC(OC)=CC=2)CC2C=CC(OC)=CC=2)[N:15]=1.[F:40][C:41]1[CH:42]=[C:43]([NH2:49])[CH:44]=[N:45][C:46]=1[O:47][CH3:48]>>[NH2:21][C:16]1[N:17]=[C:18]([CH3:20])[N:19]=[C:14]([C:3]2[CH:4]=[CH:5][C:6]([C:8]3[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=3)=[N:7][C:2]=2[NH:49][C:43]2[CH:44]=[N:45][C:46]([O:47][CH3:48])=[C:41]([F:40])[CH:42]=2)[N:15]=1Participants
3
Procedure
The title compound was prepared in an analogous manner to that described in Example 254 using 4-(6-fluoro-2,3′-bipyridin-5-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine and 5-fluoro-6-methoxypyridin-3-amine (Anichem), and was isolated as an orange amorphous solid (5.7%). m/z (ESI, +ve ion) 405.0 (M+H)+. 1H NMR (400 MHz, d6-DMSO) δ 12.03 (1H, s); 9.27 (1H, d, J=2.0 Hz); 8.91 (1H, d, J=8.2 Hz); 8.67 (1H, dd, J=4.8, 1.5 Hz); 8.55 (1H, d, J=2.2 Hz); 8.39-8.43 (1H, m); 8.36 (1H, dd, J=12.7, 2.3 Hz); 7.93 (1H, br. s.); 7.79 (1H, br. s.); 7.62 (1H, d, J=8.2 Hz); 7.57 (1H, dd, J=7.9, 4.8 Hz); 3.96 (3H, s); 2.45 (3H, s).
Sources & evidence
- ORD record
- ord-377ffd4e06df4750854c238b77e5e27c
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08772480B2
Reaction notes
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