Triethylamine → HCID 178441561, compound

HRID 326465Notes

Reaction equation

HRID 326465 reaction equation
ON1C(=O)CCC1=O.C(N(CC)CC)C.[CH2:16]([O:23][C:24](Cl)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl.[CH2:28]([C:32]1[NH:33][C:34]2[CH2:39][CH:38]([C:40]([O:42][CH3:43])=[O:41])[NH:37][CH2:36][C:35]=2[N:44]=1)[CH2:29][CH2:30][CH3:31]>CN(C)C=O>[CH2:28]([C:32]1[NH:33][C:34]2[CH2:39][CH:38]([C:40]([O:42][CH3:43])=[O:41])[N:37]([C:24]([O:23][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:25])[CH2:36][C:35]=2[N:44]=1)[CH2:29][CH2:30][CH3:31]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 10387Benzyl chloroformateHCID 80170N-HydroxysuccinimideHCID 178441560HCID 178441560, compound

Product 1

HCID 178441561HCID 178441561, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

N-Hydroxysuccinimide (0.69 g) and triethylamine (0.6 g) are dissolved in dry dimethylformamide (5 ml), and thereto is added dropwise benzyloxycarbonyl chloride (1.02 g) under ice-cooling. The mixture is stirred for 10 minutes, and thereto is added triethylamine (2.0 g). To the mixture is further added a solution of methyl 2-n-butyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-6-carboxylate hydrochloride (1.55 g) in dimethylformamide (5 ml), and the mixture is stirred at room temperature overnight. The reaction solution is concentrated under reduced pressure, and thereto are added water and chloroform. The aqueous layer is extracted with chloroform, and the extract is combined with the chloroform layer, dried, and evaporated under reduced pressure to remove the solvent. The resulting oily residue is purified by silica gel column chromatography (solvent; chloroform/methanol) to give methyl 2-n-butyl-5-benzyloxycarbonyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-6-carboxylate (1.21 g) as pale yellow oil.

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred at room temperature overnight
  3. concentrationThe reaction solution is concentrated under reduced pressure
  4. additionare added water and chloroform
  5. extractionThe aqueous layer is extracted with chloroform
  6. customdried
  7. customevaporated under reduced pressure
  8. customto remove the solvent
  9. customThe resulting oily residue is purified by silica gel column chromatography (solvent; chloroform/methanol)

Sources & evidence

ORD record
ord-c10ae69f786c44819d1cd4c5dc216bd7
Source dataset
uspto-grants-1993_12
Patent number
US05268377

Reaction notes

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