Water → N-(5-(3-(4-(bis(4-Methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-2-ylamino)pyridin-2-yl)acetamide

HRID 1621693Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1621693
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH3:8][O:9][C:10]1[CH:58]=[CH:57][C:13]([CH2:14][N:15]([CH2:48][C:49]2[CH:54]=[CH:53][C:52]([O:55][CH3:56])=[CH:51][CH:50]=2)[C:16]2[N:21]=[C:20]([CH3:22])[N:19]=[C:18]([C:23]3[C:24]([NH:40][C:41]4[CH:42]=[CH:43][C:44]([NH2:47])=[N:45][CH:46]=4)=[N:25][CH:26]=[C:27]([CH2:29][N:30]4[CH2:35][CH2:34][N:33]([S:36]([CH3:39])(=[O:38])=[O:37])[CH2:32][CH2:31]4)[CH:28]=3)[N:17]=2)=[CH:12][CH:11]=1.N1C=CC=CC=1.O>CN(C=O)C>[CH3:56][O:55][C:52]1[CH:51]=[CH:50][C:49]([CH2:48][N:15]([CH2:14][C:13]2[CH:12]=[CH:11][C:10]([O:9][CH3:8])=[CH:58][CH:57]=2)[C:16]2[N:21]=[C:20]([CH3:22])[N:19]=[C:18]([C:23]3[C:24]([NH:40][C:41]4[CH:42]=[CH:43][C:44]([NH:47][C:1](=[O:3])[CH3:2])=[N:45][CH:46]=4)=[N:25][CH:26]=[C:27]([CH2:29][N:30]4[CH2:31][CH2:32][N:33]([S:36]([CH3:39])(=[O:38])=[O:37])[CH2:34][CH2:35]4)[CH:28]=3)[N:17]=2)=[CH:54][CH:53]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 66611149N5-(3-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-2-yl)pyridine-2,5-diamine

Produkt 1

HCID 66611488N-(5-(3-(4-(bis(4-Methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-2-ylamino)pyridin-2-yl)acetamideAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Acetic anhydride (Aldrich) (0.13 mL, 1.4 mmol) was added slowly at 0° C. to a stirred solution of N5-(3-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-2-yl)pyridine-2,5-diamine (0.0864 g, 0.122 mmol) and pyridine (0.60 mL, 7.4 mmol) in DMF (2 mL). The mixture was stirred at rt for 1.5 h. Water was added and the resulting solid was collected by filtration and washed with water and air-dried to give N-(5-(3-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-2-ylamino)pyridin-2-yl)acetamide (0.0857 g, 94% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 11.86 (s, 1H); 8.72 (d, J=2.15 Hz, 1H); 8.51 (d, J=2.54 Hz, 1H); 8.24 (d, J=2.35 Hz, 1H); 8.09 (s, 1H); 7.96 (d, J=2.15 Hz, 1H); 7.91 (s, 1H); 7.20 (dd, J=8.22, 6.26 Hz, 4H); 6.86 (t, J=8.61 Hz, 4H); 4.84 (d, J=8.80 Hz, 4H); 3.80 (d, J=7.43 Hz, 6H); 3.51 (s, 2H); 3.18 (br. s., 4H); 2.71 (s, 3H); 2.60 (s, 3H); 2.55 (t, J=4.21 Hz, 4H); 2.20 (s, 3H). m/z (ESI, +ve ion) 753.0 (M+H)+.

Aufarbeitung

  1. filtrationthe resulting solid was collected by filtration
  2. washwashed with water
  3. customair-dried

Quellen und Nachweise

ORD-Eintrag
ord-481a0fd3f56f46ea91ebd8567c352d44
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772480B2

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