Methyl iodide → HCID 59448303, compound

HRID 1880230Notes

Reaction equation

HRID 1880230 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[C@@H:13]([CH2:14][NH:15][C:16]3[N:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][N:17]=3)[CH2:12][N:11]([C:26]([CH:28]3[CH2:33][CH2:32][N:31]([C:34]([C:36]4([CH3:39])[CH2:38][CH2:37]4)=[O:35])[CH2:30][CH2:29]3)=[O:27])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[H-].[Na+].[CH3:42]I>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[C@@H:13]([CH2:14][N:15]([CH3:42])[C:16]3[N:21]=[CH:20][C:19]([C:22]([F:24])([F:23])[F:25])=[CH:18][N:17]=3)[CH2:12][N:11]([C:26]([CH:28]3[CH2:29][CH2:30][N:31]([C:34]([C:36]4([CH3:39])[CH2:37][CH2:38]4)=[O:35])[CH2:32][CH2:33]3)=[O:27])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 46897742HCID 46897742, compound

Product 1

HCID 59448303HCID 59448303, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

{(3S,4S)-3-(3,4-Dichloro-phenyl)-4-[(5-trifluoromethyl-pyrimidin-2-ylamino)-methyl]-pyrrolidin-1-yl}-[1-(1-methyl-cyclopropanecarbonyl)-piperidin-4-yl]-methanone (30.0 mg, 0.051 mmol) were dissolved in DMF (1 mL) and treated with NaH (55% dispersion in oil) (2.5 mg, 0.056 mmol) at ambient temperature. After 5 min methyl iodide (3.5 μL, 0.056 mmol) were added and the reaction mixture was stirred over night. After quenching with water and extraction with ethyl acetate (3×10 mL) the combined organic phases were dried on sodium sulfate and filtered. After evaporation of the solvent the crude product was subjected to column chromatography (silica gel, ethyl acetate) to yield the title product (19 mg, 62%) as a colorless foam. ES-MS m/e: 598.3 (M+H+).

Workup

  1. customAfter quenching with water and extraction with ethyl acetate (3×10 mL) the combined organic phases
  2. customwere dried on sodium sulfate
  3. filtrationfiltered
  4. customAfter evaporation of the solvent the crude product

Sources & evidence

ORD record
ord-6bcec36617754f9e82140f7e262236df
Source dataset
uspto-grants-2012_11
Patent number
US08318759B2

Reaction notes

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