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

HRID 404756Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][CH:11]([S:14]([C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][C:25]=2[Cl:26])[C:22](=[O:27])[N:21](CC2C=CC(OC)=CC=2)[CH:20]=[CH:19]3)=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C>C(O)(C(F)(F)F)=O>[Cl:26][C:25]1[CH:24]=[C:23]2[C:18]([CH:19]=[CH:20][NH:21][C:22]2=[O:27])=[CH:17][C:16]=1[S:14]([CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)=[O:15]

Participants

Conditions

Temperature: 150 °C

Procedure

180 mg 4-[7-Chloro-2-(4-methoxy-benzyl)-1-oxo-1,2-dihydro-isoquinoline-6-sulfinyl]-piperidine-1-carboxylic acid tert-butyl ester (289) were dissolved in 2 ml of TFA and heated in a microwave at 150° C. for 40 min in total. After evaporation the mixture was dissolved in 1 N HCl and extracted with dichloromethane and lyophilized. 58 mg of 7-Chloro-6-(piperidine-4-sulfinyl)-2H-isoquinolin-1-one could be obtained as the hydrochloride. Rt=0.78 min (Method B). Detected mass: 311.1/313.1 (M+H+).

Workup

customAfter evaporation the mixture
dissolutionwas dissolved in 1 N HCl
extractionextracted with dichloromethane

Sources & evidence

ORD record: ord-2272e23fbc744375a25e8def937c2233
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748614B2

Reaction notes

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