Methyl iodide → HCID 11951837, compound

HRID 1766472Notes

Reaction equation

HRID 1766472 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([O:24][CH2:25][CH2:26][O:27][CH3:28])=[N:10][CH:11]=[C:12]([CH:23]=2)[C:13]([NH:15][C@@H:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]2[OH:22])=[O:14])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:31]I>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([O:24][CH2:25][CH2:26][O:27][CH3:28])=[N:10][CH:11]=[C:12]([CH:23]=2)[C:13]([NH:15][C@@H:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]2[O:22][CH3:31])=[O:14])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11951302HCID 11951302, compound

Product 1

HCID 11951837HCID 11951837, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 5-(4-chloro-phenyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-6-(2-methoxy-ethoxy)-nicotinamide (example 16, 50 mg) in THF (0.5 ml) was added sodium hydride dispersion (60% in mineral oil, 5.4 mg) at 0° C. The mixture was stirred at room temperature for 1 h. Methyl iodide (18.4 mg) was added and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo. The product was purified by flash chromatography (SiO2, CH2Cl2=>CH2Cl2MeOH 9:1) to give 5-(4-chloro-phenyl)-N-((1R,2R)-2-methoxy-cyclohexyl)-6-(2-methoxy-ethoxy)-nicotinamide (27 mg) as a colorless oil. MS (ISP) 419.4 (M+H)+.

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customThe product was purified by flash chromatography (SiO2, CH2Cl2=>CH2Cl2MeOH 9:1)

Sources & evidence

ORD record
ord-94d56e34a1ed4f8f93162735ca810685
Source dataset
uspto-grants-2007_06
Patent number
US07229999B2

Reaction notes

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