Water → HCID 66611145, compound

HRID 1621598Notes

Reaction equation

HRID 1621598 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:52]=[CH:51][C:8]([CH2:9][N:10]([CH2:42][C:43]2[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][CH:44]=2)[C:11]2[N:16]=[C:15]([CH3:17])[N:14]=[C:13]([C:18]3[CH:19]=[C:20]([CH2:33][N:34]([CH2:39][CH2:40][OH:41])[C:35](=[O:38])[CH2:36]Cl)[CH:21]=[N:22][C:23]=3[NH:24][C:25]3[CH:26]=[N:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=3)[N:12]=2)=[CH:7][CH:6]=1.O>C1COCC1>[CH3:3][O:4][C:5]1[CH:52]=[CH:51][C:8]([CH2:9][N:10]([CH2:42][C:43]2[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][CH:44]=2)[C:11]2[N:16]=[C:15]([CH3:17])[N:14]=[C:13]([C:18]3[CH:19]=[C:20]([CH2:33][N:34]4[CH2:39][CH2:40][O:41][CH2:36][C:35]4=[O:38])[CH:21]=[N:22][C:23]=3[NH:24][C:25]3[CH:26]=[N:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=3)[N:12]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 66610585HCID 66610585, compound

Product 1

HCID 66611145HCID 66611145, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% in mineral oil) (0.014 g, 0.346 mmol) was added to a mixture of N-((5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-((6-methoxy-3-pyridinyl)amino)-3-pyridinyl)methyl)-2-chloro-N-(2-hydroxyethyl)acetamide (0.110 g, 0.157 mmol) in 3 mL of THF at 0° C. The reaction mixture was allowed to warm up to ambient temperature. After 1 h, water was added and the mixture was extracted with EtOAc (3×). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated to give 4-((5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-((6-methoxy-3-pyridinyl)amino)-3-pyridinyl)methyl)-3-morpholinone (0.101 g, 0.152 mmol, 97% yield) as a yellow foam. 1H NMR (400 MHz, CDCl3) δ 11.66 (s, 1H); 8.71 (d, J=2.54 Hz, 1H); 8.23-8.27 (m, 1H); 8.20 (d, J=2.54 Hz, 1H); 7.89 (dd, J=8.80, 2.74 Hz, 1H); 7.15-7.24 (m, 4H); 6.80-6.90 (m, 4H); 6.70 (d, J=8.80 Hz, 1H); 4.86 (s, 2H); 4.81 (s, 2H); 4.55 (s, 2H); 4.10 (s, 2H); 3.92 (s, 3H); 3.81 (s, 3H); 3.78 (s, 3H); 3.74-3.77 (m, 2H); 3.23-3.28 (m, 2H); 2.57 (s, 3H). m/z (ESI, +ve ion) 663.2 (M+H)+.

Workup

  1. extractionthe mixture was extracted with EtOAc (3×)
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-28d7ceb279ab4687b4ee1f4aa9dff50a
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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