Acetic Acid → HCID 18439870, compound

HRID 1394123Notes

Reaction equation

HRID 1394123 reaction equation
[CH:1]1([NH:4][C:5]2[CH:6]=[C:7]3[C:12](=[CH:13][CH:14]=2)[N:11]=[C:10]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[CH:9]=[C:8]3[N:22]([CH3:24])[CH3:23])[CH2:3][CH2:2]1.[C:25](O)(=[O:27])[CH3:26].C(Cl)(=O)C.[OH-].[Na+]>C(OCC)(=O)C>[CH:1]1([N:4]([C:5]2[CH:6]=[C:7]3[C:12](=[CH:13][CH:14]=2)[N:11]=[C:10]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[CH:9]=[C:8]3[N:22]([CH3:24])[CH3:23])[C:25](=[O:27])[CH3:26])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6367Acetyl chlorideHCID 14798Sodium HydroxideHCID 18439919HCID 18439919, compound

Product 1

HCID 18439870HCID 18439870, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared by acetylation at the 6-nitrogen as follows. Into a 50 mL round-bottom flask equipped with a magnetic stirrer, condenser silicone oil bath and nitrogen inlet, was placed 750 mg (2.33 mmoles) of N6-cyclopropyl-N4,N4-dimethyl-2-[3-fluorophenyl]-4,6-quinolinediamine. To this was added 5 mL of glacial acetic acid. After the material dissolved, 202 mg (2.57 mmoles, 1.1 equiv.) of acetyl chloride was added. The mixture was stirred at room temperature for 1 hr, then heated to 60° C. for 2 hr. At the end of this time the reaction was cooled and poured into a 1 L separatory funnel containing 300 mL ethyl acetate and 500 mL of 1 N NaOH solution. The organic layer was separated, washed with NaOH solution, dried over Na2SO4, filtered and concentrated. The residue was then crystallised from methylene chloride and hexane to give 550 mg (65%) of product.

Workup

  1. customInto a 50 mL round-bottom flask equipped with a magnetic stirrer, condenser silicone oil bath and nitrogen inlet
  2. dissolutionAfter the material dissolved
  3. temperatureheated to 60° C. for 2 hr
  4. temperatureAt the end of this time the reaction was cooled
  5. additionpoured into a 1 L separatory funnel
  6. customThe organic layer was separated
  7. washwashed with NaOH solution
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was then crystallised from methylene chloride and hexane

Sources & evidence

ORD record
ord-57c914d435a841d5949438fcf7156c6c
Source dataset
uspto-grants-2008_03
Patent number
US07348340B2

Reaction notes

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