Methylamine → HCID 15979798, compound

HRID 1896361Notes

Reaction equation

HRID 1896361 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-e6ed60cc7f9e4503be556952a2482684
Source dataset
uspto-grants-2013_08
Patent number
US08518943B2

Reaction notes

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