Acetonitrile → HCID 14457604, compound

HRID 1194155Notes

Reaction equation

HRID 1194155 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH2:6]Cl.[CH3:13][O:14][C:15]([CH:17]1[N:22]([C:23](=[O:37])[CH:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:21][C:20]2[N:38](CC(=O)C3C=CC=CC=3)[CH2:39][NH:40][C:19]=2[CH2:18]1)=[O:16].C(#N)C>CCOCC>[CH3:13][O:14][C:15]([CH:17]1[N:22]([C:23](=[O:37])[CH:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:21][C:20]2[N:38]=[CH:39][N:40]([CH2:6][C:5]3[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:3]([O:2][CH3:1])[CH:4]=3)[C:19]=2[CH2:18]1)=[O:16]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 81740Veratryl chlorideHCID 21249260HCID 21249260, compound

Product 1

HCID 14457604HCID 14457604, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 1.5 g 3,4-dimethoxybenzyl chloride, 2.5 g methyl-5-diphenylacetyl-3-(2-oxo-2-phenylethyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylate and 30 mL acetonitrile is heated at reflux 16 hr. The cooled solution is added dropwise to 400 mL vigorously stirred ether and the resulting precipitate is collected by filtration. This precipitate is dissolved in 40 mL methanol and treated with 8 g zinc dust and 40 mL acetic acid. The resulting suspension is sonicated 2 hr then the solution is filtered from excess zinc. The filtrate is dissolved in 400 mL dichloromethane and treated dropwise with 450 mL 10% Na2CO3 with vigorous stirring. The organic phase is separated, dried, concentrated and the major product is isolated by chromatography on silica gel (chloroform-methanol, 99:1) as a crisp foam. NMR (CDCl3) 3.88 (s,3H,0Me); 3.80 (s,3H,0Me); 3.58 (s,3H,0Me).

Workup

  1. temperatureat reflux 16 hr
  2. filtrationthe resulting precipitate is collected by filtration
  3. dissolutionThis precipitate is dissolved in 40 mL methanol
  4. additiontreated with 8 g zinc dust and 40 mL acetic acid
  5. customThe resulting suspension is sonicated 2 hr
  6. filtrationthe solution is filtered from excess zinc
  7. dissolutionThe filtrate is dissolved in 400 mL dichloromethane
  8. additiontreated dropwise with 450 mL 10% Na2CO3 with vigorous stirring
  9. customThe organic phase is separated
  10. customdried
  11. concentrationconcentrated
  12. customthe major product is isolated by chromatography on silica gel (chloroform-methanol, 99:1) as a crisp foam

Sources & evidence

ORD record
ord-c97c0d7e7c3c475a82afe6e7e8fcf988
Source dataset
uspto-grants-1989_03
Patent number
US04812462

Reaction notes

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