Heptanoyl chloride → HCID 22320422, compound

HRID 497890

Reaction equation

HRID 497890 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[CH:11][C:10]=1[NH2:19].[C:20](Cl)(=[O:27])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>N1C=CC=CC=1>[CH3:1][S:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[CH:11][C:10]=1[NH:19][C:20](=[O:27])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

4

Reactant 2

HCID 17313Heptanoyl chlorideHCID 22320477N4-[5-(methylthio)pentyl]quinoline-3,4-diamine

Product 1

HCID 22320422HCID 22320422, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

A round bottom flask was charged with a magnetic stir bar, N4-[5-(methylthio)pentyl]quinoline-3,4-diamine (3.17 g, 11.46 mmol) and anhydrous pyridine (46 mL) under a nitrogen atmosphere. The resulting homogeneous solution was cooled to 0° C. in an ice-water bath. To the cooled solution was added neat heptanoyl chloride (1.87 g, 12.61 mmol). The reaction was judged to be complete after stirring at ambient temperature for 1 hour. The volatiles were removed under reduced pressure and the resulting oil was partitioned between chloroform and water. The layers were separated. The organic layer was washed with saturated aqueous sodium bicarbonate and brine, dried over anhydrous sodium sulfate, filtered and then concentrated under reduced pressure to afford N-(4-{[5-(methylthio)pentyl]amino}quinolin-3-yl)heptanamide (4.44 g, 11.46 mmol) which was isolated as a brown oil and used without further purification.

Workup

  1. additionA round bottom flask was charged with a magnetic stir bar
  2. customThe volatiles were removed under reduced pressure
  3. customthe resulting oil was partitioned between chloroform and water
  4. customThe layers were separated
  5. washThe organic layer was washed with saturated aqueous sodium bicarbonate and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-43dc86bfbd2642ab8c7b81251542836b
Source dataset
uspto-grants-2005_09
Patent number
US06949649B2

Linked notes

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