Water → HCID 22386552, compound

HRID 1072411Notes

Reaction equation

HRID 1072411 reaction equation
[CH2:1]([S:3][C:4]1[N:9]2[CH:10]=[CH:11][N:12]=[C:8]2[CH:7]=[C:6]([C:13]2[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[C:15]([O:23][CH3:24])[CH:14]=2)[N:5]=1)[CH3:2].[NH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.O.C(Cl)Cl>C(Cl)Cl.CO>[CH2:1]([S:3][C:4]1[N:9]2[CH:10]=[CH:11][N:12]=[C:8]2[CH:7]=[C:6]([C:13]2[CH:18]=[CH:17][C:16]([S:19]([N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)(=[O:21])=[O:20])=[C:15]([O:23][CH3:24])[CH:14]=2)[N:5]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 8082PiperidineHCID 22386549HCID 22386549, compound

Product 1

HCID 22386552HCID 22386552, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of 4-(5-Ethylsulfanyl-imidazo[1,2-c]pyrimidin-7yl)-2-methoxy-benzenesulfonylchloride (200 mg, 0.52 mmol) and piperidine (89 mg, 1.04 mmol) in CH2Cl2: MeOH (2:1, 5 ml). was stirred overnight at room temperature. Water was added to the reaction mixture and extraction was carried out with CH2Cl2. The combined organic layer was washed with brine and dried over Na2SO4. The organic layer was concentrated to give the crude product of 5-Ethylsulfanyl-7-[3-methoxy-4-(piperidine-1-sulfonyl)-phenyl]imidazo[1,2-c]pyrimidine which was purified by preparative thin layer chromatography (45 mg, 20%).

Workup

  1. washThe combined organic layer was washed with brine
  2. dry with materialdried over Na2SO4
  3. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-8fb38c178f5547a68659a865296392ab
Source dataset
uspto-grants-2005_06
Patent number
US06911443B2

Reaction notes

Loading…