Dimethylamine → HCID 90384588, compound

HRID 928681Notes

Reaction equation

HRID 928681 reaction equation
[CH3:1][NH:2][CH3:3].[Br:4][C:5]1[C:13]2[S:12][C:11]([CH2:14]Br)=[CH:10][C:9]=2[C:8]([F:16])=[C:7]([F:17])[CH:6]=1>C1COCC1.C(#N)C>[Br:4][C:5]1[C:13]2[S:12][C:11]([CH2:14][N:2]([CH3:3])[CH3:1])=[CH:10][C:9]=2[C:8]([F:16])=[C:7]([F:17])[CH:6]=1

Participants

5

Reactant 2

HCID 674DimethylamineHCID 90384332HCID 90384332, compound

Product 1

HCID 90384588HCID 90384588, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Acetonitrile (1 mL) was added to a solution (0.5 mL) of 2.0 M dimethylamine in THF, and a solution (2 mL) of the compound (121 mg, 0.354 mmol) of Step 1 of Example 65 in acetonitrile was added dropwise under ice-cooling, and stirred at room temperature overnight. The solvent was distilled away under reduced pressure. The resulting residue was diluted with ethyl acetate, washed with a saturated aqueous sodium hydrogen carbonate solution, and then dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure to thus obtain the title compound.

Workup

  1. temperaturecooling
  2. distillationThe solvent was distilled away under reduced pressure
  3. additionThe resulting residue was diluted with ethyl acetate
  4. washwashed with a saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-3aea20838292450da62a1817e0d8af5a
Source dataset
uspto-grants-2016_03
Patent number
US09290487B2

Reaction notes

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