Water → HCID 58246280, compound

HRID 1850835Notes

Reaction equation

HRID 1850835 reaction equation
C(OC([N:6]1[CH2:11][CH2:10][N:9]([S:12](=[O:39])(=[O:38])[NH:13][CH2:14][CH2:15][O:16][C:17]2[CH:26]=[C:25]3[C:20]([CH2:21][CH2:22][N:23]=[C:24]3[C:27]3([C:31]4[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=4)[CH2:30][CH2:29][CH2:28]3)=[CH:19][CH:18]=2)[CH2:8][CH2:7]1)=O)C.[OH-].[K+].O>C(O)C>[Cl:37][C:34]1[CH:33]=[CH:32][C:31]([C:27]2([C:24]3[C:25]4[C:20](=[CH:19][CH:18]=[C:17]([O:16][CH2:15][CH2:14][NH:13][S:12]([N:9]5[CH2:10][CH2:11][NH:6][CH2:7][CH2:8]5)(=[O:38])=[O:39])[CH:26]=4)[CH2:21][CH2:22][N:23]=3)[CH2:30][CH2:29][CH2:28]2)=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 58246395HCID 58246395, compound

Product 1

HCID 58246280HCID 58246280, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(2-{1-[1-(4-Chloro-phenyl)-cyclobutyl]-3,4-dihydro-isoquinolin-7-yloxy}-ethylsulfamoyl)-piperazine-1-carboxylic acid ethyl ester (450 mg, 0.782 mmol, example 54, procedure 1) and a 10% solution of potassium hydroxid in ethanol (20 ml) were heated under reflux for 15 h. The solvent was reduced and water was added to the residue. The mixture was extracted with dichloromethane. The combined organic layers were washed with sodium chloride, dried with potassium sulphate and evaporated. The residue was purified by column chromatography with silica gel using dichloromethane/methanol 3%→5% as the eluent to give the desired product as a yellow oil (394 mg, 0.782 mmol, 61%).

Workup

  1. temperatureunder reflux for 15 h
  2. extractionThe mixture was extracted with dichloromethane
  3. washThe combined organic layers were washed with sodium chloride
  4. dry with materialdried with potassium sulphate
  5. customevaporated
  6. customThe residue was purified by column chromatography with silica gel

Sources & evidence

ORD record
ord-78f15e5b28934b348d575d7099418ed3
Source dataset
uspto-grants-2015_02
Patent number
US08957089B2

Reaction notes

Loading…