Triethylamine → HCID 66765490, compound

HRID 594205Notes

Reaction equation

HRID 594205 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[NH:12][C:13](=O)[CH2:14][CH2:15][CH2:16][CH3:17].[NH2:19][O:20][CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:26](=[O:35])[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(N(CC)CC)C>CC(O)C>[CH2:14]([C:13]1[N:19]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:26](=[O:35])[O:27][CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:2]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[N:5]=[CH:4][C:3]=2[N:12]=1)[CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66765094HCID 66765094, compoundHCID 86695045Carbamic acid, N-[4-(aminooxy)butyl]-, phenylmethyl ester

Product 1

HCID 66765490HCID 66765490, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

N-(4-chloroquinolin-3-yl)valeramide (1.97 g), benzyl (4-aminooxybutyl)carbamate (2.99 g), triethylamine (0.89 g) and 2-propanol (40.69 g) were combined and heated at 80° C. for 3.5 hours. The reaction was cooled to room temperature, filtered, and the filtrate concentrated under reduced pressure. Dichloromethane (20 mL) was added to the resulting solid and the mixture was stirred for twenty minutes. Undissolved solid was removed by filtration and the filtrate was washed with two 10 mL portions of water that had been made slightly acidic by the addition of 20 drops of hydrochloric acid (1.2 M). The organic fraction was dried and concentrated under reduced pressure. The crude solid was recrystallized from tetrahydrofuran to provide 2.56 g of benzyl 4-{[2-butyl-1H-imidazo[4,5-c]quinolin-1-yl]oxy}butylcarbamate.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated under reduced pressure
  4. additionDichloromethane (20 mL) was added to the resulting solid
  5. customwas removed by filtration
  6. washthe filtrate was washed with two 10 mL portions of water that
  7. additionhad been made slightly acidic by the addition of 20 drops of hydrochloric acid (1.2 M)
  8. customThe organic fraction was dried
  9. concentrationconcentrated under reduced pressure
  10. customThe crude solid was recrystallized from tetrahydrofuran

Sources & evidence

ORD record
ord-14b40c11acd947ae9616bde801b0c9ab
Source dataset
uspto-grants-2016_01
Patent number
US09242980B2

Reaction notes

Loading…