Water → HCID 837733, compound

HRID 513437Notes

Reaction equation

HRID 513437 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[N:21]=[CH:20][CH:19]=[CH:18]2.O>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:12][C:13]2[CH:14]=[CH:15][CH:16]=[C:17]3[C:22]=2[N:21]=[CH:20][CH:19]=[CH:18]3)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 73984-Chlorobenzenesulfonyl chlorideHCID 113598-Aminoquinoline

Product 1

HCID 837733HCID 837733, compoundYield 61.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

4-Chlorobenzenesulfonyl chloride (300 mg, 1.38 mmol) was added to a stirred solution of 8-aminoquinoline (200 mg, 1.38 mmol) in pyridine (2 ml). DMAP (cat.) was added and the reaction was stirred at room temperature for 4 h. After no further progress of the reaction was observed (monitored by TLC and LCMS), water was added and the mixture was extracted with DCM. The organic phase was washed with a sat. KHSO4 solution, dried (Na2SO4) and concentrated in vacuo. The crude residue was triturated with n-hexane to give the title compound (270 mg, 61%).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with DCM
  3. washThe organic phase was washed with a sat. KHSO4 solution
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was triturated with n-hexane

Sources & evidence

ORD record
ord-cf0aaee9fef94f83aacda0711078e6dd
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

Loading…