Dimethylformamide → HCID 22036855, compound

HRID 1789779Notes

Reaction equation

HRID 1789779 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[N:12]=[C:11]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[N:10]=[C:9]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[N:8]=2)[C:5]2[CH:25]=[CH:26][CH:27]=[CH:28][C:4]=2[N:3]=1.[H-].[Na+].CN(C=O)C.Cl[CH2:37][O:38][CH:39]=[O:40]>O>[CH3:37][O:38][C:39]([NH:1][C:2]1[N:6]([C:7]2[N:8]=[C:9]([N:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)[N:10]=[C:11]([N:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)[N:12]=2)[C:5]2[CH:25]=[CH:26][CH:27]=[CH:28][C:4]=2[N:3]=1)=[O:40]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 11955792HCID 11955792, compoundHCID 17803410Chloromethyl formate

Product 1

HCID 22036855HCID 22036855, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.19 g (0.50 mmol) of 2-(2-aminobenzimidazol-1-yl)-4,6-dimorpholino-1,3,5-triazine synthesized in (1) of the Example 6 and 60% sodium hydride (24 mg, 0.60 mmol) added to DMF (2 ml) were reacted at room temperature for 1 hour. The reaction mixture was added and reacted with 0.040 ml (0.55 mmol) of chloromethylformate at room temperature for 16 hours. The reaction solution was poured into water and extracted with methyl acetate. The organic layer was separated, 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 100 mg (yield: 46%) of the titled compound as colorless crystals.

Workup

  1. customwere reacted at room temperature for 1 hour
  2. additionThe reaction mixture was added
  3. extractionextracted with methyl acetate
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-eac1321f2c99465f8fa75f66bfd88b15
Source dataset
uspto-grants-2006_07
Patent number
US07071189B2

Reaction notes

Loading…