4-Toluenesulfonyl chloride → 2-ethyl-1-(2-methylpropyl)-7-(2-morpholin-4-yl-2-oxoethoxy)-1H-imidazo[4,5-c]quinolin-4-amine

HRID 2203520Notes

Reaction equation

HRID 2203520 reaction equation
[OH-].[NH4+:2].[CH2:3]([C:5]1[N:6]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:7]2[C:16]3[CH:15]=[CH:14][C:13]([O:17][CH2:18][C:19]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[O:20])=[CH:12][C:11]=3[N+:10]([O-])=[CH:9][C:8]=2[N:28]=1)[CH3:4].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>ClCCl>[CH2:3]([C:5]1[N:6]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:7]2[C:16]3[CH:15]=[CH:14][C:13]([O:17][CH2:18][C:19]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[O:20])=[CH:12][C:11]=3[N:10]=[C:9]([NH2:2])[C:8]=2[N:28]=1)[CH3:4]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 689735912-ethyl-1-(2-methylpropyl)-7-(2-morpholin-4-yl-2-oxoethoxy)-5-oxido-1H-imidazo[4,5-c]quinoline

Product 1

HCID 588336972-ethyl-1-(2-methylpropyl)-7-(2-morpholin-4-yl-2-oxoethoxy)-1H-imidazo[4,5-c]quinolin-4-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ammonium hydroxide (0.5 mL) was added to a solution of 2-ethyl-1-(2-methylpropyl)-7-(2-morpholin-4-yl-2-oxoethoxy)-5-oxido-1H-imidazo[4,5-c]quinoline (0.53 g, 1.28 mmol) in dichloromethane (3 mL), and the mixture was cooled to 0° C. p-Toluenesulfonyl chloride (0.29 g, 1.5 mmol) was added in small portions over a period of 20 minutes. The reaction was stirred at ambient temperature overnight. The reaction mixture was partitioned between dichloromethane and 1% aqueous sodium carbonate. The organic fraction was washed with 1% aqueous sodium carbonate (2×30 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was recrystallized from ethyl acetate, isolated by filtration, washed with cold hexanes, and dried under high vacuum at 55° C. to provide 0.391 g of 2-ethyl-1-(2-methylpropyl)-7-(2-morpholin-4-yl-2-oxoethoxy)-1H-imidazo[4,5-c]quinolin-4-amine as off-white needles, mp 219-220° C.

Workup

  1. additionwas added in small portions over a period of 20 minutes
  2. customThe reaction mixture was partitioned between dichloromethane and 1% aqueous sodium carbonate
  3. washThe organic fraction was washed with 1% aqueous sodium carbonate (2×30 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was recrystallized from ethyl acetate
  8. customisolated by filtration
  9. washwashed with cold hexanes
  10. customdried under high vacuum at 55° C.

Sources & evidence

ORD record
ord-98918fd37dee4ab48df0bcdc32ff058b
Source dataset
uspto-grants-2016_06
Patent number
US09365567B2

Reaction notes

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