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

HRID 1621710
Notes
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Reaction equation

HRID 1621710 reaction equation
[CH3:1][O:2][C:3]1[CH:43]=[CH:42][C:6]([CH2:7][N:8]([CH2:33][C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=2)[C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]3[CH:17]=[C:18]([CH2:31][OH:32])[CH:19]=[N:20][C:21]=3[NH:22][C:23]3[CH:24]=[N:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=3)[N:10]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:51][S:52](Cl)(=[O:54])=[O:53].O>ClCCl>[CH3:51][S:52]([O:32][CH2:31][C:18]1[CH:19]=[N:20][C:21]([NH:22][C:23]2[CH:24]=[N:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=2)=[C:16]([C:11]2[N:10]=[C:9]([N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:43][CH:42]=3)[CH2:33][C:34]3[CH:35]=[CH:36][C:37]([O:40][CH3:41])=[CH:38][CH:39]=3)[N:14]=[C:13]([CH3:15])[N:12]=2)[CH:17]=1)(=[O:54])=[O:53]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59548440(5-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)methanol

Product 1

HCID 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
Yield 82.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

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)methanol (1.0 g, 1.725 mmol) in dichloromethane (25 mL, 1.725 mmol) was stirred at 0° C. and treated in one portion with triethylamine (1.092 mL, 7.85 mmol) and methanesulfonyl chloride (0.497 mL, 6.42 mmol). The resulting solution was stirred under nitrogen for 30 min. The reaction mixture was diluted with dichloromethane (10 mL) and treated with water (10 mL). The layers were separated and the aqueous layer was extracted with dichloromethane (2×50 mL) and dried over Na2SO4, filtered and concentrated in vacuo to give (5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)methyl methanesulfonate (0.935 g, 1.422 mmol, 82% yield). m/z (ESI, +ve ion) 658.2 (M+H)+

Workup

  1. stirringThe resulting solution was stirred under nitrogen for 30 min
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with dichloromethane (2×50 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fdfafe38883747a797f82d89a7a45826
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08772480B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes