3-(Methylsulfonyl)azetidine → 4-(2-(6-Methoxypyridin-3-Ylamino)-5-((3-(Methylsulfonyl)Azetidin-1-yl)Methyl)Pyridin-3-yl)-6-Methyl-1,3,5-Triazin-2-Amine

HRID 1621718Notes

Reaction equation

HRID 1621718 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.[CH3:44][S:45]([CH:48]1[CH2:51][NH:50][CH2:49]1)(=[O:47])=[O:46]>>[CH3:32][O:31][C:28]1[N:27]=[CH:26][C:25]([NH:24][C:17]2[C:16]([C:11]3[N:12]=[C:13]([CH3:15])[N:14]=[C:9]([NH2:8])[N:10]=3)=[CH:23][C:20]([CH2:21][N:50]3[CH2:51][CH:48]([S:45]([CH3:44])(=[O:47])=[O:46])[CH2:49]3)=[CH:19][N:18]=2)=[CH:30][CH:29]=1

Participants

3

Reactant 2

HCID 529112743-(Methylsulfonyl)azetidineHCID 601552675-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)nicotinaldehyde

Product 1

HCID 595483774-(2-(6-Methoxypyridin-3-Ylamino)-5-((3-(Methylsulfonyl)Azetidin-1-yl)Methyl)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 (0.200 g, 0.346 mmol) and 3-(methylsulfonyl)azetidine (PharmaBlock, Carrboro, N.C.) (0.070 g, 0.519 mmol). 1H NMR (400 MHz, d6-DMSO) δ 11.81 (s, 1H); 8.88 (br. s., 1H); 8.54 (d, J=2.74 Hz, 1H); 8.38 (d, J=1.76Hz, 1H); 8.13 (dd, J=8.90, 2.64 Hz, 1H); 7.77-7.94 (m, 2H); 6.85 (d, J=8.80 Hz, 1H); 4.09-4.58 (m, 7H); 3.85 (s, 3H); 3.12 (s, 3H); 2.44 (s, 3H). m/z (ESI, +ve ion) 456.8 (M+H)+.

Sources & evidence

ORD record
ord-afd43d083e7e489e97890e840440efc6
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

Loading…