5H,6H,7H,8H-(1,2,4)triazolo(1,5-a)pyrazine → 4-(5-((5,6-Dihydro-[1,2,4]triazolo[1,5-A]pyrazin-7(8H)-YL)methyl)-2-(6-methoxypyridin-3-ylamino)pyridin-3-YL)-6-methyl-1,3,5-triazin-2-amine

HRID 1812138Notes

Reaction equation

HRID 1812138 reaction equation
COC1C=CC(C[N:8](CC2C=CC(OC)=CC=2)[C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]3[C:17]([NH:24][C:25]4[CH:26]=[N:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=4)=[N:18][CH:19]=[C:20]([CH:23]=3)[CH:21]=O)[N:10]=2)=CC=1.[N:44]1[CH:45]=[N:46][N:47]2[CH2:52][CH2:51][NH:50][CH2:49][C:48]=12>>[N:44]1[CH:45]=[N:46][N:47]2[CH2:52][CH2:51][N:50]([CH2:21][C:20]3[CH:23]=[C:16]([C:11]4[N:12]=[C:13]([CH3:15])[N:14]=[C:9]([NH2:8])[N:10]=4)[C:17]([NH:24][C:25]4[CH:26]=[N:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=4)=[N:18][CH:19]=3)[CH2:49][C:48]=12

Participants

3

Reactant 2

HCID 184069195H,6H,7H,8H-(1,2,4)triazolo(1,5-a)pyrazineHCID 601552675-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)nicotinaldehyde

Product 1

HCID 497855214-(5-((5,6-Dihydro-[1,2,4]triazolo[1,5-A]pyrazin-7(8H)-YL)methyl)-2-(6-methoxypyridin-3-ylamino)pyridin-3-YL)-6-methyl-1,3,5-triazin-2-amine

Procedure

The title compound was synthesized following an analogous procedure to Example 220 using 5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)nicotinaldehyde (178 mg, 0.308 mmol) and 5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyrazine (GeneTech, Indianapolis, Ind.) (57.4 mg, 0.462 mmol). 1H NMR (400 MHz, CDCl3) δ 11.70 (s, 1H); 8.78 (d, J=2.54 Hz, 1H); 8.36 (d, J=2.74 Hz, 1H); 8.25 (d, J=2.35 Hz, 1H); 8.10 (dd, J=8.80, 2.74 Hz, 1H); 7.87 (s, 1H); 6.78 (d, J=8.61 Hz, 1H); 5.59 (s, 2H); 4.20 (t, J=5.38 Hz, 2H); 3.94 (s, 3H); 3.84 (s, 2H); 3.73 (s, 2H); 3.00 (t, J=5.48 Hz, 2H); 2.56 (s, 3H). m/z (ESI, +ve ion) 445.9 (M+H)+.

Sources & evidence

ORD record
ord-776083f861764179b44f370154b6eba3
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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