Acetyl chloride → HCID 178441544, compound

HRID 21855Notes

Reaction equation

HRID 21855 reaction equation
[CH2:1]([C:5]1[N:17]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]3[NH:35][N:34]=[N:33][N:32]=3)=[CH:21][CH:20]=2)[C:8]2[CH:9]([C:13]([O:15][CH3:16])=[O:14])[NH:10][CH2:11][CH2:12][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.[C:43](Cl)(=[O:45])[CH3:44]>C(Cl)(Cl)Cl>[C:43]([N:10]1[CH2:11][CH2:12][C:7]2[N:6]=[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])[N:17]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[C:31]4[NH:35][N:34]=[N:33][N:32]=4)=[CH:21][CH:20]=3)[C:8]=2[CH:9]1[C:13]([O:15][CH3:16])=[O:14])(=[O:45])[CH3:44]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 178441543HCID 178441543, compound

Product 1

HCID 178441544HCID 178441544, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a mixture of the compound obtained in Example 3 (296 mg), triethylamine (317 mg) and chloroform (10 ml) is added dropwise a solution of acetyl chloride (148 mg) in chloroform (1 ml) under ice-cooling. The mixture is stirred at room temperature for two hours, and the reaction solution is washed, dried and evaporated to remove the solvent. The resulting residue is purified by silica gel column chromatography (solvent; chloroform/methanol=30:1) to give methyl 5-acetyl-2-n-butyl-3-[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-4-carboxylate (158 mg).

Workup

  1. temperaturecooling
  2. washthe reaction solution is washed
  3. customdried
  4. customevaporated
  5. customto remove the solvent
  6. customThe resulting residue is purified by silica gel column chromatography (solvent; chloroform/methanol=30:1)

Sources & evidence

ORD record
ord-5f16e14073e445939883754d00bfab26
Source dataset
uspto-grants-1995_06
Patent number
US05424316

Reaction notes

Loading…