5-Chloro-6-methoxypyridin-3-amine → HCID 66611452, compound

HRID 1812044Notes

Reaction equation

HRID 1812044 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:10])[CH:5]=[N:6][C:7]=1[O:8][CH3:9].F[C:12]1[C:17]([C:18]2[N:23]=[C:22]([CH3:24])[N:21]=[C:20]([N:25]([CH2:35][C:36]3[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=3)[CH2:26][C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)[N:19]=2)=[CH:16][CH:15]=[CH:14][N:13]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:12]2[C:17]([C:18]3[N:23]=[C:22]([CH3:24])[N:21]=[C:20]([N:25]([CH2:26][C:27]4[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=4)[CH2:35][C:36]4[CH:37]=[CH:38][C:39]([O:42][CH3:43])=[CH:40][CH:41]=4)[N:19]=3)=[CH:16][CH:15]=[CH:14][N:13]=2)[CH:5]=[N:6][C:7]=1[O:8][CH3:9]

Participants

3

Reactant 2

HCID 573702345-Chloro-6-methoxypyridin-3-amineHCID 595482404-(2-fluoropyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

Product 1

HCID 66611452HCID 66611452, compound

Procedure

The title compound was prepared in an analogous manner to that described in Example 164 using 5-chloro-6-methoxypyridin-3-amine and 4-(2-fluoropyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine, and isolated as a brown oil (100%). 1H NMR (400 MHz, d6-DMSO) δ 11.71 (s, 1H); 8.78 (dd, J=7.8, 2.2 Hz, 1H); 8.33 (dd, J=4.7, 2.0 Hz, 1H); 8.26 (d, J=2.5 Hz, 1H); 8.19 (d, J=2.3 Hz, 1H); 7.17-7.29 (m, 4H); 6.82-6.96 (m, 5H); 4.81 (d, J=6.5 Hz, 4H); 3.91 (s, 3H); 3.74 (s, 3H); 3.70 (s, 3H); 2.55-2.58 (m, 3H). m/z (ESI, +ve ion) 584.0 (M+H)+.

Sources & evidence

ORD record
ord-c3b014536f104a7ab95d559589204ced
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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