4-Toluenesulfonyl chloride → HCID 66900711, compound

HRID 1520416Notes

Reaction equation

HRID 1520416 reaction equation
[CH2:1]([C:3]1[N:4]([CH2:17][CH2:18][CH2:19][CH2:20][N:21]([CH:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N+:8]([O-])=[CH:7][C:6]=2[N:16]=1)[CH3:2].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[OH-].[NH4+:47]>C(Cl)(Cl)Cl>[NH2:47][C:7]1[C:6]2[N:16]=[C:3]([CH2:1][CH3:2])[N:4]([CH2:17][CH2:18][CH2:19][CH2:20][N:21]([CH:29]3[CH2:30][CH2:31][O:32][CH2:33][CH2:34]3)[C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:25])[CH3:27])[C:5]=2[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:8]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 67431480tert-butyl [4-(2-ethyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)butyl]tetrahydro-2H-pyran-4-ylcarbamate

Product 1

HCID 66900711HCID 66900711, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of tert-butyl [4-(2-ethyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)butyl]tetrahydro-2H-pyran-4-ylcarbamate in chloroform was added p-toluene sulfonyl chloride (1.2 eq.) followed by aq.ammonium hydroxide solution. The resulting reaction mixture was stirred at room temperature for overnight. Reaction mixture was washed with saturated sodium bicarbonate solution. Organic layer separated, dried over anhydrous sodium sulphate and concentrated under reduced pressure to yield sticky solid, which was then purified using silica gel column chromatography to afford tert-butyl [4-(4-amino-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]tetrahydro-2H-pyran-4-ylcarbamate.

Workup

  1. customThe resulting reaction mixture
  2. customReaction mixture
  3. washwas washed with saturated sodium bicarbonate solution
  4. customOrganic layer separated
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customto yield sticky solid, which
  8. customwas then purified

Sources & evidence

ORD record
ord-056f3b88ddc14986b2c8d1e579c851d3
Source dataset
uspto-grants-2015_07
Patent number
US09073913B2

Reaction notes

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