Water → N-[2-(4-amino-7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide

HRID 598291Notes

Reaction equation

HRID 598291 reaction equation
[OH-].[NH4+:2].[CH2:3]([O:10][C:11]1[CH:12]=[CH:13][C:14]2[C:15]3[N:24]([CH2:25][C:26]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])([CH3:28])[CH3:27])[C:23]([CH2:34][O:35][CH2:36][CH3:37])=[N:22][C:16]=3[CH:17]=[N+:18]([O-])[C:19]=2[CH:20]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.O>ClCCl.C(Cl)(Cl)Cl.CO>[NH2:2][C:17]1[C:16]2[N:22]=[C:23]([CH2:34][O:35][CH2:36][CH3:37])[N:24]([CH2:25][C:26]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])([CH3:28])[CH3:27])[C:15]=2[C:14]2[CH:13]=[CH:12][C:11]([O:10][CH2:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)=[CH:20][C:19]=2[N:18]=1

Participants

8

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 67051025N-[2-(7-benzyloxy-2-ethoxymethyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide

Product 1

HCID 57545342N-[2-(4-amino-7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Concentrated ammonium hydroxide (3 to 4 mL) was added to a solution of N-[2-(7-benzyloxy-2-ethoxymethyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide (1.75 g, 3.51 mmol) in dichloromethane (35 mL) with rapid stirring. p-Toluenesulfonyl chloride (670 mg, 3.51 mmol) was added. The reaction was stirred for one hour; a precipitate formed. Water (100 mL) was added, and the dichloromethane was removed under reduced pressure. Dichloromethane (5 mL) was then added with rapid stirring, and the resulting powder was isolated by filtration and dissolved in 90:10 chloroform:methanol (200 mL). The resulting solution was concentrated under reduced pressure, and the residue was triturated with hot propyl acetate (50 mL), isolated by filtration, and dried under reduced pressure to provide 1.45 g of N-[2-(4-amino-7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide as a tan powder.

Workup

  1. customa precipitate formed
  2. customthe dichloromethane was removed under reduced pressure
  3. additionDichloromethane (5 mL) was then added with rapid stirring
  4. customthe resulting powder was isolated by filtration
  5. concentrationThe resulting solution was concentrated under reduced pressure
  6. customthe residue was triturated with hot propyl acetate (50 mL)
  7. customisolated by filtration
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-983c7f523d4444a1afa071b305c7f8c6
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

Loading…