Dabco → HCID 68007175, compound

HRID 1027789Notes

Reaction equation

HRID 1027789 reaction equation
[CH2:1]([NH:3][CH3:4])[CH3:2].ClC(Cl)(O[C:9](=[O:15])OC(Cl)(Cl)Cl)Cl.[CH3:17][N:18]1[C:26](=[O:27])[NH:25][C:24]2[C:19]1=[N:20][C:21]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[N:22][CH:23]=2.N12CCN(CC1)CC2>ClCCl.C(N(CC)CC)C>[CH2:1]([N:3]([CH3:4])[C:9]([N:25]1[C:24]2[C:19](=[N:20][C:21]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[N:22][CH:23]=2)[N:18]([CH3:17])[C:26]1=[O:27])=[O:15])[CH3:2]

Participants

7

Reactant 4

HCID 9237DabcoHCID 12219N-MethylethylamineHCID 94429TriphosgeneHCID 15462514HCID 15462514, compound

Product 1

HCID 68007175HCID 68007175, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of N-ethylmethylamine (78 mg) and triphosgene (209 mg) in dichloromethane (10 ml) was added dropwise triethylamine (365 μl) at room temperature and the mixture was stirred for 10 minutes. To the reaction mixture was added a solution of 9-methyl-2-phenyl-7,9-dihydro-8H-purine-8-one <the compound of Reference Example 21> (200 mg) and 1,4-diazabicyclo[2.2.2]octane (220 mg) in dichloromethane (10 ml) and the mixture was stirred for 1 hour. The reaction mixture was washed with water and the organic layer was, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=100/0˜0/100) to give the title compound 156 mg.

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. washThe reaction mixture was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=100/0˜0/100)

Sources & evidence

ORD record
ord-e4199f8b5601441d92d5c365573cacfc
Source dataset
uspto-grants-2014_05
Patent number
US08735406B2

Reaction notes

Loading…