Acetyl chloride → HCID 57691413, compound

HRID 548604Notes

Reaction equation

HRID 548604 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].Cl.Cl.[NH:7]1[CH2:12][CH2:11][CH:10]([CH2:13][CH2:14][NH:15][C:16]2[N:17]([CH2:30][CH2:31][CH3:32])[N:18]=[C:19]3[C:28]=2[C:27]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[N:21]=[C:20]3[NH2:29])[CH2:9][CH2:8]1.C(N(CC)CC)C.CN1CCCC1=O>ClCCl>[C:1]([N:7]1[CH2:8][CH2:9][CH:10]([CH2:13][CH2:14][NH:15][C:16]2[N:17]([CH2:30][CH2:31][CH3:32])[N:18]=[C:19]3[C:28]=2[C:27]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[N:21]=[C:20]3[NH2:29])[CH2:11][CH2:12]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6367Acetyl chloride2×HCID 8471TriethylamineHCID 13387N-methyl-2-pyrrolidoneHCID 86630221HCID 86630221, compound

Product 1

HCID 57691413HCID 57691413, compoundYield 21.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (0.27 g, 0.24 mL, 3.39 mmol) was added to a stirring suspension of N1-(2-piperidin-4-ylethyl)-2-propyl-2H-pyrazolo[3,4-c]quinoline-1,4-diamine dihydrochloride (1.2 g, 2.83 mmol) and triethylamine (2.9 g, 3.9 mL, 28.3 mmol) in dichloromethane (100 mL). After 10 minutes, 1-methyl-2-pyrrolidinone (15 mL) was added and the resulting suspension was stirred at ambient temperature 16 hours. Additional acetyl chloride (0.27 g, 0.24 mL, 3.39 mmol) was added and the suspension was stirred at ambient temperature 4 hours. The dichloromethane was removed under reduced pressure and water (100 mL) was added to the resulting oil. The solution was transferred to a separatory funnel and extracted with ethyl acetate (2×50 mL) and dichloromethane (50 mL). The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Methanol (20 mL) and sodium hydroxide (10 mL, 1 N in water) were added to the resulting oil and the suspension was stirred one hour. The methanol was removed under reduced pressure and the aqueous layer was neutralized with hydrochloric acid (1 N in water) and extracted with dichloromethane (3×50 mL). The combined organic fractions were dried over magnesium sulfate, filtered and concentrated under reduced pressure to 7.5 g of a yellow oil. Sodium carbonate (75 mL, 10% w/w in water) was added to this oil and a brown gum crashed out and stuck to the sides of the flask. The liquid was decanted off and the remaining gum was crystallized from hot acetonitrile (50 mL) and isolated by filtration to yield 242 mg of N1-[2-(1-acetylpiperidin-4-yl)ethyl]-2-propyl-2H-pyrazolo[3,4-c]quinoline-1,4-diamine as a tan solid. mp 203-206° C. Anal. calcd for C22H30N6O: C, 66.98; H, 7.66; N, 21.30. Found: C, 66.92; H, 7.92; N, 21.57.

Workup

  1. stirringthe suspension was stirred at ambient temperature 4 hours
  2. customThe dichloromethane was removed under reduced pressure and water (100 mL)
  3. additionwas added to the resulting oil
  4. customThe solution was transferred to a separatory funnel
  5. extractionextracted with ethyl acetate (2×50 mL) and dichloromethane (50 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. additionMethanol (20 mL) and sodium hydroxide (10 mL, 1 N in water) were added to the resulting oil
  10. stirringthe suspension was stirred one hour
  11. customThe methanol was removed under reduced pressure
  12. extractionextracted with dichloromethane (3×50 mL)
  13. dry with materialThe combined organic fractions were dried over magnesium sulfate
  14. filtrationfiltered
  15. concentrationconcentrated under reduced pressure to 7.5 g of a yellow oil
  16. additionSodium carbonate (75 mL, 10% w/w in water) was added to this oil
  17. customThe liquid was decanted off
  18. customthe remaining gum was crystallized from hot acetonitrile (50 mL)
  19. customisolated by filtration

Sources & evidence

ORD record
ord-bc10785f4afc41cbab49ad9c3354b6f7
Source dataset
uspto-grants-2011_05
Patent number
US07943610B2

Reaction notes

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