Ammonia → N-{2-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}methanesulfonamide

HRID 81883Notes

Reaction equation

HRID 81883 reaction equation
Cl[C:2]1[C:11]([NH:12][C:13](=O)[CH2:14][CH2:15][O:16][CH3:17])=[C:10]([NH:19][CH2:20][C:21]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])([CH3:23])[CH3:22])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.N.ClC1C(NC(=O)CCOC)=C(CC(NS(C)(=O)=O)(C)C)C2C(=CC=CC=2)[N:32]=1>CO>[NH2:32][C:2]1[C:11]2[N:12]=[C:13]([CH2:14][CH2:15][O:16][CH3:17])[N:19]([CH2:20][C:21]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])([CH3:22])[CH3:23])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 222Ammonia2×HCID 86626601N-{2-chloro-4-[2-(methanesulfonylamino)-2-methylpropyl]aminoquinolin-3-yl}-3-methoxypropionamideHCID 86626602N-{2-chloro-4-[2-(methanesulfonylamino)-2-methylpropyl]quinolin-3-yl}-3-methoxypropionamide

Product 1

HCID 10000533N-{2-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}methanesulfonamideYield 167.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
170 °C

Procedure

A Parr bomb was charged with 25.0 g of N-{2-chloro-4-[2-(methanesulfonylamino)-2-methylpropyl]aminoquinolin-3-yl}-3-methoxypropionamide and ammonia in methanol (300 mL of 7 N). A second vessel was charged with 30.21 g of N-{2-chloro-4-[2-(methanesulfonylamino)-2-methylpropyl]quinolin-3-yl}-3-methoxypropionamide and ammonia in methanol (400 mL of 7 N). Both vessels were sealed and then heated at 170° C. for 14 hours. The reaction mixtures were combined and the solvent was removed under reduced pressure. The residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate. The organic layer was washed sequentially with saturated aqueous sodium bicarbonate and brine, dried over sodium sulfate, filtered, and then concentrated under reduced pressure to provide 38.16 g of N-{2-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}methanesulfonamide as an off white foam.

Workup

  1. customBoth vessels were sealed
  2. customThe reaction mixtures
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate
  5. washThe organic layer was washed sequentially with saturated aqueous sodium bicarbonate and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f442abd5d9ae46e8b46ebdf2f73ebd2c
Source dataset
uspto-grants-2014_09
Patent number
US08846710B2

Reaction notes

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