Dimethylamine → HCID 22050407, compound

HRID 1866958Notes

Reaction equation

HRID 1866958 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([N:9]2[C:14]([CH3:15])=[CH:13][C:12]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=3[F:25])=[CH:11][C:10]2=[O:26])[CH:6]=[CH:7][CH:8]=1.[CH3:27][NH:28][CH3:29]>CO>[F:25][C:19]1[CH:20]=[C:21]([F:24])[CH:22]=[CH:23][C:18]=1[CH2:17][O:16][C:12]1[CH:13]=[C:14]([CH3:15])[N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([CH2:2][N:28]([CH3:29])[CH3:27])[CH:4]=2)[C:10](=[O:26])[CH:11]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 22050008HCID 22050008, compound

Product 1

HCID 22050407HCID 22050407, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-[3-(chloromethyl)phenyl]-4-[(2,4-difluorobenzyl)oxy]-6-methylpyridin-2(1H)-one (from step 1 of the synthesis of EXAMPLE 293) (0.500 g, 1.330 mmol) was suspended in a stock solution of N,N-dimethylamine in methanol (2.0 mL, 2.0 M) and stirred overnight at room temperature. Reaction was concentrated and the residue partitioned between H2O (25 mL) and ethyl acetate (25 mL). The aqueous layer was further extracted with ethyl acetate (2×30 ml), and the combined organics were washed with brine (30 mL), dried over MgSO4, and concentrated to afford an off-white solid (0.508 g, 99%).

Workup

  1. customReaction
  2. concentrationwas concentrated
  3. customthe residue partitioned between H2O (25 mL) and ethyl acetate (25 mL)
  4. extractionThe aqueous layer was further extracted with ethyl acetate (2×30 ml)
  5. washthe combined organics were washed with brine (30 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b968e592af9f4544bd01510bdd109a4a
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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