Ethanolamine → 2-((5-(4-Amino-6-methyl-1,3,5-triazin-2-YL)-6-(6-methoxypyridin-3-ylamino)pyridin-3-YL)methylamino)ethanol

HRID 1812129Notes

Reaction equation

HRID 1812129 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.[CH2:44]([CH2:46][NH2:47])[OH:45]>>[NH2:8][C:9]1[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]2[CH:23]=[C:20]([CH2:21][NH:47][CH2:46][CH2:44][OH:45])[CH:19]=[N:18][C:17]=2[NH:24][C:25]2[CH:26]=[N:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)[N:10]=1

Participants

3

Reactant 2

HCID 700EthanolamineHCID 601552675-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)nicotinaldehyde

Product 1

HCID 595481672-((5-(4-Amino-6-methyl-1,3,5-triazin-2-YL)-6-(6-methoxypyridin-3-ylamino)pyridin-3-YL)methylamino)ethanol

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 (0.200 g, 0.346 mmol) and ethanolamine (Aldrich, St. Louis, Mo.) (0.031 mL, 0.519 mmol). 1H NMR (400 MHz, d6-DMSO) δ 11.79 (s, 1H); 8.89 (d, J=2.35 Hz, 1H); 8.55 (d, J=2.54 Hz, 1H); 8.34 (d, J=2.35 Hz, 1H); 8.13 (dd, J=8.90, 2.64 Hz, 1H); 7.74-7.93 (m, 1H); 6.84 (d, J=9.00 Hz, 1H); 5.08 (br. s., 1H); 4.08 (s, 2H); 3.82-3.88 (m, 3H); 3.63 (q, J=4.96 Hz, 2H); 2.95 (t, J=5.09 Hz, 2H); 2.44 (s, 3H). m/z (ESI, +ve ion) 383.1 (M+H)+.

Sources & evidence

ORD record
ord-f51083702e524fa5a0a5ae7dc303d249
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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