5-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)nicotinaldehyde → 4-((5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)(hydroxy)methyl)-N,N-dimethylbenzenesulfonamide

HRID 1812144Notes

Reaction equation

HRID 1812144 reaction equation
[CH3:1][N:2]([CH3:14])[S:3]([C:6]1[CH:11]=[CH:10][C:9]([Mg]Br)=[CH:8][CH:7]=1)(=[O:5])=[O:4].[CH3:15][O:16][C:17]1[CH:57]=[CH:56][C:20]([CH2:21][N:22]([CH2:47][C:48]2[CH:53]=[CH:52][C:51]([O:54][CH3:55])=[CH:50][CH:49]=2)[C:23]2[N:28]=[C:27]([CH3:29])[N:26]=[C:25]([C:30]3[C:31]([NH:38][C:39]4[CH:40]=[N:41][C:42]([O:45][CH3:46])=[CH:43][CH:44]=4)=[N:32][CH:33]=[C:34]([CH:37]=3)[CH:35]=[O:36])[N:24]=2)=[CH:19][CH:18]=1>>[CH3:55][O:54][C:51]1[CH:50]=[CH:49][C:48]([CH2:47][N:22]([CH2:21][C:20]2[CH:19]=[CH:18][C:17]([O:16][CH3:15])=[CH:57][CH:56]=2)[C:23]2[N:28]=[C:27]([CH3:29])[N:26]=[C:25]([C:30]3[CH:37]=[C:34]([CH:35]([OH:36])[C:9]4[CH:10]=[CH:11][C:6]([S:3]([N:2]([CH3:14])[CH3:1])(=[O:5])=[O:4])=[CH:7][CH:8]=4)[CH:33]=[N:32][C:31]=3[NH:38][C:39]3[CH:40]=[N:41][C:42]([O:45][CH3:46])=[CH:43][CH:44]=3)[N:24]=2)=[CH:53][CH:52]=1

Participants

3

Reactant 2

HCID 601552675-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)nicotinaldehydeHCID 178486139HCID 178486139, compound

Product 1

HCID 666120144-((5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)(hydroxy)methyl)-N,N-dimethylbenzenesulfonamideYield 73.8%

Procedure

(4-(N,N-Dimethylsulfamoyl)phenyl)magnesium bromide (0.48 M in THF) (2545 μL, 1.222 mmol) was added to 5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)nicotinaldehyde (176.4 mg, 0.305 mmol) to give a deep orange solution. The solution was stirred for 16 h and then quenched with MeOH (1.0 mL). The product was extracted into DCM from water, dried (MgSO4), and purified by flash chromatography (0 to 10% to 20% to 30% EtOAc/DCM) to give 4-((5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)(hydroxy)methyl)-N,N-dimethylbenzenesulfonamide (171.5 mg, 0.225 mmol, 73.6% yield) as a yellow solid. 1H NMR (400 MHz, d6-DMSO) δ 11.51 (s, 1H); 8.74 (s, 1H); 8.30 (dd, J=4.11, 2.54 Hz, 2H); 7.85 (d, J=2.35 Hz, 1H); 7.55-7.72 (m, 4H); 7.26 (d, J=8.22 Hz, 2H); 7.19 (d, J=8.41 Hz, 2H); 6.90 (d, J=8.41 Hz, 2H); 6.83 (d, J=8.61 Hz, 2H); 6.74 (d, J=9.00 Hz, 1H); 6.19 (d, J=3.91 Hz, 1H); 5.86 (d, J=4.11 Hz, 1H); 4.68-4.91 (m, 4H); 3.82 (s, 3H); 3.74 (s, 3H); 3.70 (s, 3H); 2.56 (s, 6H); 2.54 (s, 3H). m/z (ESI, +ve ion) 763.1 (M+H)+.

Workup

  1. customto give a deep orange solution
  2. customquenched with MeOH (1.0 mL)
  3. extractionThe product was extracted into DCM from water
  4. dry with materialdried (MgSO4)
  5. custompurified by flash chromatography (0 to 10% to 20% to 30% EtOAc/DCM)

Sources & evidence

ORD record
ord-7ddafb052f5641ac8551aa6ac2502c26
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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