Morpholine → HCID 66600185, compound

HRID 1812006Notes

Reaction equation

HRID 1812006 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]([CH:31]=[O: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.[Na+].[NH:47]1[CH2:52][CH2:51][O:50][CH2:49][CH2:48]1>C1COCC1.[O-2].[Mn+4].[O-2]>[CH3:41][O:40][C:37]1[CH:36]=[CH:35][C:34]([CH2:33][N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:43][CH:42]=2)[C:9]2[N:10]=[C:11]([C:16]3[C:21]([NH:22][C:23]4[CH:24]=[N:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=4)=[N:20][CH:19]=[C:18]([C:31]([N:47]4[CH2:52][CH2:51][O:50][CH2:49][CH2:48]4)=[O:32])[CH:17]=3)[N:12]=[C:13]([CH3:15])[N:14]=2)=[CH:39][CH:38]=1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 8929Sodium CyanideHCID 601552675-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)nicotinaldehyde

Product 1

HCID 66600185HCID 66600185, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-((6-methoxy-3-pyridinyl)amino)-3-pyridinecarbaldehyde (0.127 g, 0.220 mmol) in THF (2.00 mL) was treated with sodium cyanide (10.77 mg, 0.220 mmol), morpholine (0.096 mL, 1.099 mmol) and manganese(IV) oxide (0.287 g, 3.30 mmol) at ambient temperature. After 30 min, more manganese(IV) oxide (0.287 g, 3.30 mmol) was added and the mixture was stirred overnight at ambient temperature. The mixture was filtered through Celite® (diatomaceous earth) and the organic layer was washed with water followed by saturated NaCl (aq.) and then dried over anhydrous Na2SO4, filtered and concentrated to give N,N-bis(4-methoxybenzyl)-4-(2-((6-methoxy-3-pyridinyl)amino)-5-(4-morpholinylcarbonyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine (0.128 g, 0.193 mmol, 88% yield) as a brown foam. 1H NMR (400 MHz, CDCl3) δ 11.95 (s, 1H); 8.90 (d, J=2.54 Hz, 1H); 8.39 (d, J=2.35 Hz, 1H); 8.28 (d, J=2.74 Hz, 1H); 7.89 (dd, J=8.80, 2.74 Hz, 1H); 7.13-7.24 (m, 4H); 6.81-6.90 (m, 4H); 6.73 (d, J=8.80 Hz, 1H); 4.85 (s, 2H); 4.82 (s, 2H); 3.94 (s, 3H); 3.81 (s, 3H); 3.78 (s, 3H); 3.57-3.69 (m, 8H); 2.59 (s, 3H). m/z (ESI, +ve ion) 663.2 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through Celite® (diatomaceous earth)
  2. washthe organic layer was washed with water
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-65ab5b1618e34a0e89ec9b78eb6dc56f
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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