Methylamine → HCID 69506817, compound

HRID 2366660Notes

Reaction equation

HRID 2366660 reaction equation
[CH2:1]([C:4]1[N:5]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28](OCC)=[O:29])[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:16]=1)[CH2:2][CH3:3].C1COCC1.[CH3:38][NH2:39]>O>[CH3:38][NH:39][C:28](=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][N:5]1[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:16]=[C:4]1[CH2:1][CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 57447053HCID 57447053, compound

Product 1

HCID 69506817HCID 69506817, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl 12-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)dodecanoate (4.0 g, 9.1 mmol), THF (5 mL), and methylamine (available as a 40% solution in water, 8 mL) was sealed in a high-pressure vessel and heated at 80° C. overnight. The solvent was removed under reduced pressure, and the residue was dissolved in dichloromethane. The resulting solution was washed sequentially with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 3.8 g of N-methyl-12-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)dodecanamide.

Workup

  1. customwas sealed in a high-pressure vessel
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in dichloromethane
  4. washThe resulting solution was washed sequentially with saturated aqueous sodium bicarbonate and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6ee9ace9a1094ae0a8101c82eb3544e6
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

Loading…