Methyl iodide → HCID 59448301, compound

HRID 1880231Notes

Reaction equation

HRID 1880231 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]([C:28]3[CH:33]=[C:32]([CH3:34])[N:31]=[N:30][CH:29]=3)=[O:27])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[H-].[Na+].[CH3:37]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]([CH3:37])[C:16]3[N:17]=[CH:18][C:19]([C:22]([F:24])([F:25])[F:23])=[CH:20][N:21]=3)[CH2:12][N:11]([C:26]([C:28]3[CH:33]=[C:32]([CH3:34])[N:31]=[N:30][CH:29]=3)=[O:27])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 46853843HCID 46853843, compound

Product 1

HCID 59448301HCID 59448301, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

{(3S,4S)-3-(3,4-Dichloro-phenyl)-4-[(5-trifluoromethyl-pyrimidin-2-ylamino)-methyl]-pyrrolidin-1-yl)-(6-methyl-pyridazin-4-yl)-methanone (50.0 mg, 0.1 mmol) were dissolved in DMF (1 mL) and treated with NaH (55% dispersion in oil) (5 mg, 0.11 mmol) at ambient temperature. After 5 min methyl iodide (7.3 μL, 0.12 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, dichloro methane, dichloro methane/methanol 4:1) to yield the title product (30 mg, 58%) as a brown foam. ES-MS m/e: 525.2 (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-1a1069a4fe94496d9828164f4d359e72
Source dataset
uspto-grants-2012_11
Patent number
US08318759B2

Reaction notes

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