Dichloromethane → HCID 10692084, compound

HRID 1068567Notes

Reaction equation

HRID 1068567 reaction equation
[N:1]1([C:10]2[N:15]=[C:14](Cl)[N:13]=[C:12]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[N:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].[CH3:29][C@H:30]1[O:35][C@@H:34]([CH3:36])[CH2:33][NH:32][CH2:31]1.ClCCl>CN(C=O)C.O>[N:1]1([C:10]2[N:15]=[C:14]([N:32]3[CH2:31][C@@H:30]([CH3:29])[O:35][C@@H:34]([CH3:36])[CH2:33]3)[N:13]=[C:12]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[N:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 6415002,6-Dimethylmorpholine, cis-HCID 107342282-(Benzimidazol-1-yl)-4-chloro-6-morpholino-1,3,5-triazine

Product 1

HCID 10692084HCID 10692084, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The obtained 2-(benzimidazol-1-yl)-4-chloro-6-morpholino-1,3,5-triazine (320 mg, 1.0 mmol) dissolved in DMF (20 ml) was added with potassium carbonate (430 mg, 3.2 mmol) and cis-2,6-dimethylmorpholine (140 mg, 1.2 mmol) and stirred at room temperature for 45 minutes. The reaction mixture was condensed under reduced pressure and the obtained residue was added with dichloromethane and water and shaken for mixing. The separated organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography to obtain 360 mg (yield: 90%) of the titled compound as colorless crystals.

Workup

  1. customcondensed under reduced pressure
  2. stirringshaken
  3. additionfor mixing
  4. washThe separated organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-123ffe505673438aae8d2c6fca113a2c
Source dataset
uspto-grants-2001_06
Patent number
US06251900B1

Reaction notes

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