Diethyl Ether → HCID 22346319, compound

HRID 897288Notes

Reaction equation

HRID 897288 reaction equation
C([O:9][C:10]1[C:11]([C:22]([O:24]C)=O)=[N:12][C:13]([C:20]#[N:21])=[C:14]2[C:19]=1[N:18]=[CH:17][CH:16]=[CH:15]2)(=O)C1C=CC=CC=1.[CH3:26][O:27][C:28]1[C:35]([O:36][CH3:37])=[CH:34][CH:33]=[CH:32][C:29]=1[CH2:30][NH2:31].CCOCC>C1(C)C=CC=CC=1>[C:20]([C:13]1[N:12]=[C:11]([C:22]([NH:31][CH2:30][C:29]2[CH:32]=[CH:33][CH:34]=[C:35]([O:36][CH3:37])[C:28]=2[O:27][CH3:26])=[O:24])[C:10]([OH:9])=[C:19]2[C:14]=1[CH:15]=[CH:16][CH:17]=[N:18]2)#[N:21]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 781062,3-DimethoxybenzylamineHCID 22346422HCID 22346422, compound

Product 1

HCID 22346319HCID 22346319, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of methyl 8-(benzoyloxy)-5-cyano-1,6-naphthyridine-7-carboxylate (264 mg, 0.792 mmol) in anhydrous toluene (12 ml) was added 2,3-dimethoxybenzyl amine (132 mg, 0.79 mmol) and the solution was stirred at reflux under argon overnight. The solvent was removed under reduced pressure to give a brown syrup which was subsequently taken up into ether (10 ml). After stirring for 4 hours the solids were collected by vacuum filtration and dried overnight on an aberhalden to give an off white solid.

Workup

  1. temperatureat reflux under argon overnight
  2. customThe solvent was removed under reduced pressure
  3. customto give a brown syrup which
  4. stirringAfter stirring for 4 hours the solids
  5. filtrationwere collected by vacuum filtration
  6. customdried overnight on an aberhalden
  7. customto give an off white solid

Sources & evidence

ORD record
ord-61b5b9768742462db93a0db1ba6ef7b1
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

Loading…