Water → HCID 5009224, compound

HRID 513423Notes

Reaction equation

HRID 513423 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[Br:12][C:13]1[CH:22]=[CH:21][C:20]([NH2:23])=[C:19]2[C:14]=1[CH:15]=[CH:16][CH:17]=[N:18]2.N1C=CC=CC=1.O>C(Cl)Cl>[Br:12][C:13]1[CH:22]=[CH:21][C:20]([NH:23][S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])=[C:19]2[C:14]=1[CH:15]=[CH:16][CH:17]=[N:18]2

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 161927485-Bromoquinolin-8-amine--hydrogen chloride (1/1)

Product 1

HCID 5009224HCID 5009224, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzenesulfonyl chloride (72 μl, 0.57 mmol) was added to a solution of 5-bromoquinolin-8-ylamine hydrochloride (84 mg, 0.38 mmol) in pyridine (150 μl, 1.89 mmol) and DCM (5 ml) and the mixture was stirred at room temperature for 20 h. Water (5 ml) was added and the organic phase was separated. The aqueous phase was extracted with DCM and the combined organic phases were dried (MgSO4) and concentrated in vacuo. The crude residue was purified by trituration from DMSO/MeOH (1:2) to give the title compound (60 mg, 44%).

Workup

  1. customthe organic phase was separated
  2. extractionThe aqueous phase was extracted with DCM
  3. dry with materialthe combined organic phases were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by trituration from DMSO/MeOH (1:2)

Sources & evidence

ORD record
ord-beee8d37a37d43bd876739c3115b66ea
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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