Methyl iodide → HCID 86754431, compound

HRID 1586237Notes

Reaction equation

HRID 1586237 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:9]([CH2:13][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[S:28]([NH:31][C:32]([CH3:35])([CH3:34])[CH3:33])(=[O:30])=[O:29])=[CH:18][CH:17]=2)[CH3:15])[CH2:10][CH2:11][OH:12])[CH:6]=[CH:7][CH:8]=1)#[N:2].[H-].[Na+].I[CH3:39]>C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]([N:9]([CH2:13][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[S:28]([NH:31][C:32]([CH3:34])([CH3:33])[CH3:35])(=[O:30])=[O:29])=[CH:18][CH:17]=2)[CH3:15])[CH2:10][CH2:11][O:12][CH3:39])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 70065294HCID 70065294, compound

Product 1

HCID 86754431HCID 86754431, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Part A. N-[3-(cyano)phenyl]-N-[2-[2'-(1,1-dimethylethylaminosulfonyl)[1,1'-biphenyl]-4-yl]propyl]-N-2-(hydroxy)ethylamine (1.00 gm, 2.89 mmol) was dissolved in 100 mL of anhydrous THF followed by the addition of NaH (60% dispersion in mineral oil, 0.23 gm, 5.78 mmol). Once the evolution of gas ceased, iodomethane was added (0.411, 0.18 mL, 2.89 mmol) and the solution was allowed to stir overnight at room temperature. The solution was quenched with dilute HCl, and the volatiles removed in vacuum. N-[3-(Cyano)phenyl]-N-[2-[2'-(1,1-dimethylethylaminosulfonyl)[1,1'-biphenyl]-4-yl]propyl]-N-2-(methoxy)ethylamine was isolated after HPLC purification on Vydac C-18 column eluting with solvent A (acetonitrile:water:TFA 80:20:0.2) and solvent B (water:TFA 99.8:0.2) used as a gradient, as a clear oil (0.100 gm, 7%). MS m/e 506.4 (M+H)+.

Workup

  1. customThe solution was quenched with dilute HCl
  2. customthe volatiles removed in vacuum

Sources & evidence

ORD record
ord-0a305a2942164aad971cc19f8ad8cf0f
Source dataset
uspto-grants-1999_08
Patent number
US05942544

Reaction notes

Loading…