Methyl iodide → HCID 86683441, compound

HRID 2174942Notes

Reaction equation

HRID 2174942 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[NH:12][C:13](=[N:23][C:24]#[N:25])[N:14]([C:15]4[CH:16]=[N:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=4)[C:5]=3[C:4]=2[CH:3]=1.[H-].[Na+].[CH3:28]I>CN(C=O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([CH3:28])[C:13](=[N:23][C:24]#[N:25])[N:14]([C:15]4[CH:16]=[N:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=4)[C:5]=3[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178492025HCID 178492025, compound2×

Product 1

HCID 86683441HCID 86683441, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(8-bromo-1-(6-methoxypyridin-3-yl)-1H-imidazo[4,5-c]quinolin-2(3H)-ylidene)cyanamide (compound of step 4, 0.674 mmol) in 5 ml of dry DMF at 0° C. was added NaH (60% dispersed in mineral oil, 1.011 mmol). The reaction mixture was stirred for 15 minutes followed by addition of methyl iodide (1.011 mmol). Reaction mixture was stirred at 0° C. for another 1 h and quenched with water. The solvent was removed; aqueous layer was extracted with DCM. Organic layer was dried over anhydrous Na2SO4, concentrated under vacuum and purified (silica gel column, MeOH/CHCl3 as eluent) to obtain the title compound. 1H NMR (300 MHz, DMSO-d6): δ 9.27 (s, 1H), 8.62 (d, J=3 Hz, 1H), 8.37 (d, J=1.8 Hz, 1H), 8.18 (dd, J=9 Hz, 3 Hz, 1H), 8.08 (d, J=9 Hz, 1H), 7.80 (dd, J=9 Hz, 3 Hz, 1H), 7.21 (d, J=9 Hz, 1H), 7.03 (d, J=3 Hz, 1H), 4.01 (s, 3H), 3.83 (s, 3H); MS (m/z): 409 (M+1)+.

Workup

  1. customReaction mixture
  2. stirringwas stirred at 0° C. for another 1 h
  3. customquenched with water
  4. customThe solvent was removed
  5. extractionaqueous layer was extracted with DCM
  6. dry with materialOrganic layer was dried over anhydrous Na2SO4
  7. concentrationconcentrated under vacuum
  8. custompurified (silica gel column, MeOH/CHCl3 as eluent)

Sources & evidence

ORD record
ord-7524e0cd3eb742589fb6bc2c57fa3dcb
Source dataset
uspto-grants-2015_06
Patent number
US09062046B2

Reaction notes

Loading…