Methylamine → HCID 15979798, compound

HRID 1924224Notes

Reaction equation

HRID 1924224 reaction equation
Cl[C:2]1[S:3][C:4]([CH2:7][N:8]2[CH2:12][CH:11]([C:13]3[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([F:20])[C:14]=3[F:21])[CH2:10][C:9]2=[O:22])=[CH:5][N:6]=1.C[O-].[Na+].[CH3:26][NH2:27]>CO>[CH3:26][NH:27][C:2]1[S:3][C:4]([CH2:7][N:8]2[CH2:12][CH:11]([C:13]3[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([F:20])[C:14]=3[F:21])[CH2:10][C:9]2=[O:22])=[CH:5][N:6]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 10942334Sodium MethoxideHCID 57742995HCID 57742995, compound

Product 1

HCID 15979798HCID 15979798, compoundYield 180.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
95 °C

Procedure

In a 50 ml sealed vessel, 1-[(2-chloro-1,3-thiazol-5-yl)methyl]-4-(2,3,5-trifluorophenyl)pyrrolidin-2-one 250 (0.1 g, 0.3 mmol) is dissolved in MeOH (3 ml). Sodium methoxide (3 mg, 0.06 mmol) and a solution of methylamine (0.09 g, 3 mmol) in MeOH are added. The vessel is closed and heated to 95° C. for 48 h. The reaction mixture is cooled to room temperature, the solvent is evaporated and the residue is taken up in CH2Cl2 and water. The aqueous phase is extracted twice with CH2Cl2, the combined organic phases are washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The crude product is recrystallized from AcOEt to afford 185 mg of 1-{[2-(methylamino)-1,3-thiazol-5-yl]methyl}-4-(2,3,5-trifluorophenyl)pyrrolidin-2-one 252.

Workup

  1. customIn a 50 ml sealed vessel
  2. customThe vessel is closed
  3. temperatureThe reaction mixture is cooled to room temperature
  4. customthe solvent is evaporated
  5. extractionThe aqueous phase is extracted twice with CH2Cl2
  6. washthe combined organic phases are washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude product is recrystallized from AcOEt

Sources & evidence

ORD record
ord-f1091d699b8b4f3a9df2a86e4a5b5931
Source dataset
uspto-grants-2012_05
Patent number
US08178533B2

Reaction notes

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