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 1621736Notes

Reaction equation

HRID 1621736 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=9.00Hz, 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-33e38faf724c4c8381eea6f78e0304bf
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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