Triethylamine → HCID 21075818, compound

HRID 1373884Notes

Reaction equation

HRID 1373884 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:9][CH:8]=[CH:7][CH:6]=2.C(N(CC)CC)C.[C:28](Cl)(=O)[CH2:29][CH2:30][CH2:31][CH3:32]>C(Cl)Cl>[CH2:29]([C:28]1[N:12]([NH:13][C:14](=[O:15])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=1)[CH2:30][CH2:31][CH3:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61186Valeryl chlorideHCID 21075823tert-butyl N'-(3-aminoquinolin-4-yl)hydrazinecarboxylate

Product 1

HCID 21075818HCID 21075818, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl N′-(3-aminoquinolin-4-yl)hydrazinecarboxylate (2.18 g, 7.96 mmol) in 80 mL of anhydrous CH2Cl2 was cooled to 0° C. and treated with triethylamine (1.12 mL, 8.00 mmol) and valeryl chloride (0.95 mL, 8.00 mmol) under an atmosphere of nitrogen. After stirring for 3 h, the reaction mixture was concentrated under reduced pressure and the residue was treated with Et2O and filtered. The filtrate was concentrated and the resulting black tar was dissolved in 80 mL of ethanol and treated with 3 mL of triethylamine and the mixture was refluxed overnight. The reaction mixture was concentrated under reduced pressure. Chromatography (SiO2, 1–5% methanol (MeOH)/CHCl3) gave tert-butyl N-(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)carbamate (1.41 g) as a mauve foam.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was treated with Et2O
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. dissolutionthe resulting black tar was dissolved in 80 mL of ethanol
  6. additiontreated with 3 mL of triethylamine
  7. temperaturethe mixture was refluxed overnight
  8. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e3bebd15ccd84ea2a08fa60f7a156bab
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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