Methyl iodide → HCID 70873983, compound

HRID 2208757Notes

Reaction equation

HRID 2208757 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12]1[C:13]([CH3:23])=[C:14]([CH:19]=[C:20]([Cl:22])[CH:21]=1)[C:15]([O:17][CH3:18])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:24](=O)([O-])[O-].[Cs+].[Cs+].CI>C(#N)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][N:11]([CH3:24])[C:12]1[C:13]([CH3:23])=[C:14]([CH:19]=[C:20]([Cl:22])[CH:21]=1)[C:15]([O:17][CH3:18])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 70873963HCID 70873963, compound

Product 1

HCID 70873983HCID 70873983, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of methyl 3-((2-((tert-butoxycarbonyl)amino)ethyl)amino)-5-chloro-2-methylbenzoate (0.5 g, 1.46 mmol) in acetonitrile (10 mL), cesium carbonate (0.95 g, 2.92 mmol) and methyl iodide (1 g, 7.3 mmol) were added and the resulting reaction mixture heated at 80° C. for 12 h. On completion, the reaction mixture was cooled to room temperature and filtered, the residue washed with ethyl acetate and the filtrate concentrated before purification by column chromatography to afford desired product (0.325 g, 62%).

Workup

  1. customthe resulting reaction mixture
  2. temperatureOn completion, the reaction mixture was cooled to room temperature
  3. filtrationfiltered
  4. washthe residue washed with ethyl acetate
  5. concentrationthe filtrate concentrated before purification by column chromatography

Sources & evidence

ORD record
ord-64f7097f0196467d8ad57b763db86880
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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