Dimethylformamide → N-(5-(diethylamino)pentan-2-yl)-3-(6-formyl-3,4-dihydroquinolin-1(2H)-yl)propanamide

HRID 1773008Notes

Reaction equation

HRID 1773008 reaction equation
O=P(Cl)(Cl)Cl.[CH2:6]([N:8]([CH2:29][CH3:30])[CH2:9][CH2:10][CH2:11][CH:12]([NH:14][C:15](=[O:28])[CH2:16][CH2:17][N:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21][CH2:20][CH2:19]1)[CH3:13])[CH3:7].CN([CH:34]=[O:35])C>>[CH2:29]([N:8]([CH2:6][CH3:7])[CH2:9][CH2:10][CH2:11][CH:12]([NH:14][C:15](=[O:28])[CH2:16][CH2:17][N:18]1[C:27]2[C:22](=[CH:23][C:24]([CH:34]=[O:35])=[CH:25][CH:26]=2)[CH2:21][CH2:20][CH2:19]1)[CH3:13])[CH3:30]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 59237981N-(5-(diethylamino)pentan-2-yl)-3-(3,4-dihydroquinolin-1(2H)-yl)propanamide

Product 1

HCID 59237974N-(5-(diethylamino)pentan-2-yl)-3-(6-formyl-3,4-dihydroquinolin-1(2H)-yl)propanamide

Conditions

Temperature
110 °C

Procedure

POCl3 (2.37 g, 15.3 mmol) was added dropwise to DMF (1.8 mL) which was cooled in an ice bath. The combined mixture was stirred for 30 minutes and to this a solution of Compound 5 (2.64 g, 7.6 mmol) in DMF (25 mL) was added dropwise over a period of 20 min. After the addition was complete, the ice bath was removed and the reaction mixture was stirred at room temperature for 17 hour. An aqueous solution of sodium acetate (25% w/w, 25 mL) was then added to the reaction mixture and it was heated in an oil bath (T=110° C.) for 15 min. The reaction mixture was cooled and pH was adjusted with 10 N NaOH to ˜11. It was diluted with water (100 mL) and extracted with ethyl acetate. The organic layer was washed twice with water (75 mL) followed by brine (3×50 mL), dried over magnesium sulfate and then evaporated to dryness to yield 1.44 g of an orange viscous liquid which was used without any further purification. The structure of Compound 6 is given below:

Workup

  1. temperaturewas cooled in an ice bath
  2. additionAfter the addition
  3. customthe ice bath was removed
  4. stirringthe reaction mixture was stirred at room temperature for 17 hour
  5. additionAn aqueous solution of sodium acetate (25% w/w, 25 mL) was then added to the reaction mixture and it
  6. temperatureThe reaction mixture was cooled
  7. additionIt was diluted with water (100 mL)
  8. extractionextracted with ethyl acetate
  9. washThe organic layer was washed twice with water (75 mL)
  10. dry with materialdried over magnesium sulfate
  11. customevaporated to dryness

Sources & evidence

ORD record
ord-d92e680e1bfa41dda4d1265dcf1ead71
Source dataset
uspto-grants-2016_02
Patent number
US09250249B2

Reaction notes

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