3-(methylsulfonyl)pyrrolidine → (RAC)-4-(2-(6-Methoxypyridin-3-Ylamino)-5-((3-(Methylsulfonyl)Pyrrolidin-1-yl)Methyl)Pyridin-3-yl)-6-Methyl-1,3,5-Triazin-2-Amine

HRID 1621723Notes

Reaction equation

HRID 1621723 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[CH2:52][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][CH2:52][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 34193563-(methylsulfonyl)pyrrolidineHCID 601552675-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)nicotinaldehyde

Product 1

HCID 59548349(RAC)-4-(2-(6-Methoxypyridin-3-Ylamino)-5-((3-(Methylsulfonyl)Pyrrolidin-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 (0.23 g, 0.398 mmol) and 3-(methylsulfonyl)pyrrolidine (PharmaBlock, Carrboro, N.C.) (0.089 g, 0.597 mmol). 1H NMR (400 MHz, CDCl3) δ 11.63 (s, 1H); 8.73 (d, J=2.35 Hz, 1H); 8.36 (d, J=2.54 Hz, 1H); 8.21 (d, J=2.15 Hz, 1H); 8.10 (dd, J=8.80, 2.74 Hz, 1H); 6.78 (d, J=8.80 Hz, 1H); 5.55 (br. s., 2H); 3.94 (s, 3H); 3.56-3.68 (m, 3H); 2.99-3.05 (m, 1H); 2.88-2.95 (m, 1H); 2.87 (s, 3H); 2.76-2.84 (m, 1H); 2.61-2.70 (m, 1H); 2.56 (s, 3H); 2.25-2.35 (m, 2H). m/z (ESI, +ve ion) 470.9 (M+H)+.

Sources & evidence

ORD record
ord-860843ad763a47f08bcd49f5f140e4e0
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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