Hexanoyl chloride → HCID 118451589, compound

HRID 522844Notes

Reaction equation

HRID 522844 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][C:14]([CH3:17])([OH:16])[CH3:15])=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:18](Cl)(=O)[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>ClCCl>[CH3:15][C:14]([OH:16])([CH3:17])[CH2:13][N:12]1[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=[C:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

4

Reactant 2

HCID 67340Hexanoyl chloride2×HCID 149869411-((3-Aminoquinolin-4-yl)amino)-2-methylpropan-2-ol

Product 1

HCID 118451589HCID 118451589, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(3-aminoquinolin-4-ylamino)-2-methylpropan-2-ol (CAN 129655-59-0, 0.94 g, 4.06 mmol) in dichloromethane (9.5 mL) in an inert atmosphere was added dropwise with stirring at room temperature over a period of 6 min a solution of hexanoyl chloride (422 μl, 4.47 mmol) in dichloromethane (6.4 mL). After 3 h additional hexanoyl chloride (192 μl, 2.03 mmol) was added and stirring continued for another hour and finally the mixture was concentrated in vacuo. The residue was re-dissolved in ethanol (13.5 mL) and, after addition of sodiumhydroxide solution (1 M, 10.8 mL) the mixture was heated with stirring in argon to 90° C. After 75 min the mixture was allowed to cool to room temperature and concentrated in vacuo. The residue was stirred with ethyl acetate (30 mL) and water (5 mL) dried by filtration over ChemElut® and ethyl acetate was removed in vacuo. The residue was purified by flash chromatography (silica gel-NH2, 0% to 100% ethyl acetate in heptane) to give the title compound (747 mg, 89%) as yellow oil; LC-MS (UV peak area, ESI) 95%, 312.2 (MH+).

Workup

  1. waitcontinued for another hour
  2. concentrationfinally the mixture was concentrated in vacuo
  3. dissolutionThe residue was re-dissolved in ethanol (13.5 mL)
  4. additionafter addition of sodiumhydroxide solution (1 M, 10.8 mL) the mixture
  5. temperaturewas heated
  6. stirringwith stirring in argon to 90° C
  7. concentrationconcentrated in vacuo
  8. stirringThe residue was stirred with ethyl acetate (30 mL) and water (5 mL)
  9. dry with materialdried by filtration over ChemElut® and ethyl acetate
  10. customwas removed in vacuo
  11. customThe residue was purified by flash chromatography (silica gel-NH2, 0% to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-bf0b6d6391af47dd90f615c66865eab3
Source dataset
uspto-grants-2016_05
Patent number
US09334268B2

Reaction notes

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