4-[7-Chloro-2-(4-methoxy-benzyl)-1-oxo-1,2-dihydro-isoquinolin-6-ylsulfanyl]-piperidine-1-carboxylic acid tert-butyl ester → 7-Chloro-6-(piperidin-4-ylsulfanyl)-2H-isoquinolin-1-one

HRID 404753Notes

Reaction equation

HRID 404753 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([S:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][C:24]=2[Cl:25])[C:21](=[O:26])[N:20](CC2C=CC(OC)=CC=2)[CH:19]=[CH:18]3)[CH2:10][CH2:9]1)=O)(C)(C)C>C(O)(C(F)(F)F)=O>[Cl:25][C:24]1[CH:23]=[C:22]2[C:17]([CH:18]=[CH:19][NH:20][C:21]2=[O:26])=[CH:16][C:15]=1[S:14][CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

3

Reactant 1

HCID 592906794-[7-Chloro-2-(4-methoxy-benzyl)-1-oxo-1,2-dihydro-isoquinolin-6-ylsulfanyl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 592907827-Chloro-6-(piperidin-4-ylsulfanyl)-2H-isoquinolin-1-oneYield 73.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

188 mg 4-[7-Chloro-2-(4-methoxy-benzyl)-1-oxo-1,2-dihydro-isoquinolin-6-ylsulfanyl]-piperidine-1-carboxylic acid tert-butyl ester (285) in 2 ml TFA were heated in the microwave at 150° C. for 1.5 h. After evaporation the residue is taken up in 1N HCl and extracted with dichloromethane and lyophilized. 79 mg of 7-Chloro-6-(piperidin-4-ylsulfanyl)-2H-isoquinolin-1-one could be obtained as the hydrochloride. Rt=0.93 min (Method B). Detected mass: 295.1/297.1 (M+H+).

Workup

  1. customAfter evaporation the residue
  2. extractionextracted with dichloromethane

Sources & evidence

ORD record
ord-0cee0b262e76406da95305fa3943e7d9
Source dataset
uspto-grants-2014_06
Patent number
US08748614B2

Reaction notes

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