4-(5-chloro-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine → (r)-Tert-butyl 4-((5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)methyl)-3-methylpiperazine-1-carboxylate

HRID 1812022Notes

Reaction equation

HRID 1812022 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][B-](F)(F)F)[C@H:10]([CH3:19])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[K+].Cl[C:22]1[CH:23]=[C:24]([C:37]2[N:42]=[C:41]([CH3:43])[N:40]=[C:39]([N:44]([CH2:54][C:55]3[CH:60]=[CH:59][C:58]([O:61][CH3:62])=[CH:57][CH:56]=3)[CH2:45][C:46]3[CH:51]=[CH:50][C:49]([O:52][CH3:53])=[CH:48][CH:47]=3)[N:38]=2)[C:25]([NH:28][C:29]2[CH:30]=[N:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=2)=[N:26][CH:27]=1>>[CH3:53][O:52][C:49]1[CH:48]=[CH:47][C:46]([CH2:45][N:44]([CH2:54][C:55]2[CH:56]=[CH:57][C:58]([O:61][CH3:62])=[CH:59][CH:60]=2)[C:39]2[N:40]=[C:41]([CH3:43])[N:42]=[C:37]([C:24]3[CH:23]=[C:22]([CH2:14][N:11]4[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][C@H:10]4[CH3:19])[CH:27]=[N:26][C:25]=3[NH:28][C:29]3[CH:30]=[N:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=3)[N:38]=2)=[CH:51][CH:50]=1

Participants

3

Reactant 2

HCID 666119674-(5-chloro-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amineHCID 71501915potassium (R)-((4-(tert-butoxycarbonyl)-2-methylpiperazin-1-yl)methyl)trifluoroborate

Product 1

HCID 68517931(r)-Tert-butyl 4-((5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)methyl)-3-methylpiperazine-1-carboxylateYield 74.3%

Procedure

The title compound was prepared in an analogous manner to that described above in Example 157, Step 1, using potassium (R)-((4-(tert-butoxycarbonyl)-2-methylpiperazin-1-yl)methyl)trifluoroborate and 4-(5-chloro-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine to give (R)-tert-butyl 4-((5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)methyl)-3-methylpiperazine-1-carboxylate (188 mg, 0.247 mmol, 74.3% yield) as a yellow syrup. m/z (ESI, +ve ion) 761.7 (M+H)+.

Workup

  1. customThe title compound was prepared in an analogous manner to that

Sources & evidence

ORD record
ord-37b925da7aef450e9c80319d54e309a2
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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