4-Toluenesulfonyl chloride → 3-(4-Amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propan-1-ol

HRID 2090240Notes

Reaction equation

HRID 2090240 reaction equation
C1(C)C=CC(S(Cl)(=O)=O)=CC=1.C([O:18][CH2:19][CH2:20][CH2:21][N:22]1[C:34]2[C:33]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[N+:27]([O-])=[CH:26][C:25]=2[N:24]=[C:23]1[CH2:36][CH2:37][CH2:38][CH3:39])(=O)CCCC.[OH-].[NH4+:41]>C(Cl)Cl>[NH2:41][C:26]1[C:25]2[N:24]=[C:23]([CH2:36][CH2:37][CH2:38][CH3:39])[N:22]([CH2:21][CH2:20][CH2:19][OH:18])[C:34]=2[C:33]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[N:27]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 684324413-(2-Butyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)propyl pentanoate

Product 1

HCID 684322443-(4-Amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

p-Toluenesulphonyl chloride (0.93 g) was added portionwise to a vigourously stirred mixture of the product from step (iv) (1.77 g) in DCM (50 mL) and ammonium hydroxide solution (35%, 5 mL) at rt. The reaction mixture was stirred for 3 h then partitioned between water/DCM. The organics were washed with saturated NaHCO3 solution, water, dried, and the solvent evaporated under reduced pressure. The residue was dissolved in MeOH (40 mL), water (20 mL) then 6M NaOH solution (2 mL) added and the mixture stirred at rt for 18 h. The solid formed was filtered off washed with water and dried, yield 965 mg.

Workup

  1. customthen partitioned between water/DCM
  2. washThe organics were washed with saturated NaHCO3 solution, water
  3. customdried
  4. customthe solvent evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in MeOH (40 mL)
  6. additionwater (20 mL) then 6M NaOH solution (2 mL) added
  7. stirringthe mixture stirred at rt for 18 h
  8. customThe solid formed
  9. filtrationwas filtered off
  10. washwashed with water
  11. customdried

Sources & evidence

ORD record
ord-95a80336fae649349799cd86c6703075
Source dataset
uspto-grants-2013_05
Patent number
US08436178B2

Reaction notes

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