Methanol → 1-((5-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)methyl)piperidin-4-ol

HRID 1621711Notes

Reaction equation

HRID 1621711 reaction equation
CS(O[CH2:6][C:7]1[CH:8]=[N:9][C:10]([NH:39][C:40]2[CH:41]=[N:42][C:43]([O:46][CH3:47])=[CH:44][CH:45]=2)=[C:11]([C:13]2[N:18]=[C:17]([N:19]([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=3)[CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[N:16]=[C:15]([CH3:38])[N:14]=2)[CH:12]=1)(=O)=O.[OH:48][CH:49]1[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]1.C(N(CC)CC)C.CO>ClCCl.O>[CH3:28][O:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][N:19]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)[C:17]2[N:16]=[C:15]([CH3:38])[N:14]=[C:13]([C:11]3[CH:12]=[C:7]([CH2:6][N:52]4[CH2:53][CH2:54][CH:49]([OH:48])[CH2:50][CH2:51]4)[CH:8]=[N:9][C:10]=3[NH:39][C:40]3[CH:41]=[N:42][C:43]([O:46][CH3:47])=[CH:44][CH:45]=3)[N:18]=2)=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 79341Piperidin-4-olHCID 59548272(5-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)methyl methanesulfonate

Product 1

HCID 595482541-((5-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)methyl)piperidin-4-olYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A suspension of (5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)methyl methanesulfonate (0.510 g, 0.775 mmol), 4-hydroxypiperidine (0.254 g, 2.51 mmol) and triethylamine (0.491 mL, 3.53 mmol) in dichloromethane (25 mL) was stirred at room temperature overnight. The reaction mixture was diluted with water (20 mL) and extracted with dichloromethane (3×25 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep pre-packed silica gel column (40 g) eluting with a gradient of 5% to 20% 2 M NH3.MeOH in CH2Cl2 to give 1-((5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)methyl)piperidin-4-ol (0.385 g, 0.581 mmol, 74.9% yield). m/z (ESI, +ve ion) 663.3 (M+H)+.

Workup

  1. extractionextracted with dichloromethane (3×25 mL)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed through a Redi-Sep pre-packed silica gel column (40 g)
  6. washeluting with a gradient of 5% to 20% 2 M NH3

Sources & evidence

ORD record
ord-bb4181deda084e8b83d0ed1024633e1a
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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