Methyl iodide → HCID 178497030, compound

HRID 2208775Notes

Reaction equation

HRID 2208775 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:13][C@H:14]2[CH2:19][CH2:18][C@H:17]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16][CH2:15]2)[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[C:28](=O)([O-])[O-].[Cs+].[Cs+].CI>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([N:13]([C@H:14]2[CH2:19][CH2:18][C@H:17]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16][CH2:15]2)[CH3:28])[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 178497031HCID 178497031, compound

Product 1

HCID 178497030HCID 178497030, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of trans-methyl 5-bromo-3-((4-((tert-butoxycarbonyl)amino)cyclohexyl)amino)-2-methylbenzoate (3 g, 6.81 mmol) in acetonitrile (40 mL), cesium carbonate (4.4 g, 13.62 mmol) and methyl iodide (4.83 g, 34.05 mmol) were added; the resulting reaction mixture was heated at 80° C. for 7 h. Upon completion, the reaction mixture was cooled to room temperature and filtered, the residue was washed with ethyl acetate and filtrate was concentrated to afford desired crude compound which then purified by column chromatography giving the desired compound (1.3 g, 43%).

Workup

  1. customthe resulting reaction mixture
  2. temperatureUpon completion, the reaction mixture was cooled to room temperature
  3. filtrationfiltered
  4. washthe residue was washed with ethyl acetate and filtrate
  5. concentrationwas concentrated
  6. customto afford desired crude compound which
  7. customthen purified by column chromatography

Sources & evidence

ORD record
ord-3d8645ad590646aeb145c8a3630ff988
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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