Dimethylformamide → HCID 70984742, compound

HRID 339059Notes

Reaction equation

HRID 339059 reaction equation
[H-].[Na+].CN(C)C=O.[CH:8]([O:10][C:11]([CH3:46])([CH3:45])[CH2:12][O:13][C:14]1[CH:15]=[C:16](F)[CH:17]=[C:18]2[C:23]=1[N:22]=[C:21]([C:24]1N3C=C([C@@H](N4CC[C@H](N)C4)C(F)(F)F)C=CC3=NN=1)[CH:20]=[CH:19]2)=O.IC>O>[CH3:8][O:10][C:11]([CH3:46])([CH3:45])[CH2:12][O:13][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:23]=1[N:22]=[C:21]([CH3:24])[CH:20]=[CH:19]2

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 89913360HCID 89913360, compound

Product 1

HCID 70984742HCID 70984742, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of sodium hydride (60% in mineral oil; 0.013 g, 0.32 mmol) in anhydrous dimethylformamide (1.4 mL, 0.22 mmol) was added dropwise a solution of 2-methyl-1-(2-methylquinolin-8-yloxy)propan-2-ol (Example 259; 0.050 g, 0.22 mmol) in anhydrous dimethylformamide (1.4 mL, 0.22 mmol). The mixture was allowed to stir at ambient temperature for 30 minutes before by addition of iodomethane (0.054 mL, 0.86 mmol), and the resultant mixture allowed to stir at ambient temperature for 12 hours. The reaction mixture was poured into water (20 mL) and extracted with ethyl acetate (2×40 mL). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by reverse phase chromatography on a C18 column (0-100% acetonitrile/water) providing the title compound (0.038 g, 73%).

Workup

  1. extractionextracted with ethyl acetate (2×40 mL)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by reverse phase chromatography on a C18 column (0-100% acetonitrile/water)

Sources & evidence

ORD record
ord-a07d5f395f7f4ae69094ea1a0156b3da
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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