Acetonitrile → HCID 14403637, compound

HRID 1195013Notes

Reaction equation

HRID 1195013 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]Br.[CH3:10][O:11][C:12]([CH:14]1[N:19]([C:20](=[O:34])[CH:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:18][C:17]2[N:35](CC(=O)C3C=CC=CC=3)[CH2:36][NH:37][C:16]=2[CH2:15]1)=[O:13].C(#N)C>CCOCC>[CH3:10][O:11][C:12]([CH:14]1[N:19]([C:20](=[O:34])[CH:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:18][C:17]2[N:35]=[CH:36][N:37]([CH2:5][C:4]3[CH:7]=[CH:8][CH:9]=[C:2]([CH3:1])[CH:3]=3)[C:16]=2[CH2:15]1)=[O:13]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 12099m-Xylyl bromideHCID 21249260HCID 21249260, compound

Product 1

HCID 14403637HCID 14403637, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 2.7 mL 3-methylbenzyl bromide, 5.0 g methyl-5-diphenylacetyl-3-(2-oxo-2-phenylethyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylate and 50 mL acetonitrile is heated at reflux 4 hr. The cooled solution is added dropwise to 750 mL vigorously stirred ether and the resulting precipitate is collected by filtration. This precipitate is dissolved in 75 mL methanol and treated with 16 g zinc dust and 75 mL acetic acid. The resulting suspension is sonicated 6 hr then the solution is filtered from excess zinc. The filtrate is dissolved in 400 mL dichloromethane and treated dropwise with 650 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, 99.5:0.5) as a crisp foam. NMR (CDCl3) 4.97 (s, 2H, NCH2Ar).

Workup

  1. temperatureat reflux 4 hr
  2. filtrationthe resulting precipitate is collected by filtration
  3. dissolutionThis precipitate is dissolved in 75 mL methanol
  4. additiontreated with 16 g zinc dust and 75 mL acetic acid
  5. customThe resulting suspension is sonicated 6 hr
  6. filtrationthe solution is filtered from excess zinc
  7. dissolutionThe filtrate is dissolved in 400 mL dichloromethane
  8. additiontreated dropwise with 650 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, 99.5:0.5) as a crisp foam

Sources & evidence

ORD record
ord-03e92d964d3c48f191c956ba8e5deca6
Source dataset
uspto-grants-1989_03
Patent number
US04816463

Reaction notes

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