Methanol → HCID 178484836, compound

HRID 2402600Notes

Reaction equation

COC1C=CC(C[N:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH:19]4[CH2:24][CH2:23][CH:22]([NH:25][CH3:26])[CH2:21][CH2:20]4)[CH:14]=3)[C:9]2=[O:27])=CC=1.CO>C(O)(C(F)(F)F)=O>[CH3:26][NH:25][C@H:22]1[CH2:23][CH2:24][C@H:19]([O:18][C:13]2[CH:14]=[C:15]3[C:10](=[CH:11][CH:12]=2)[C:9](=[O:27])[NH:8][CH:17]=[CH:16]3)[CH2:20][CH2:21]1

Participants

Conditions

Temperature: 150 °C

Procedure

2.46 g of 2-(4-methoxy-benzyl)-6-(4-methylamino-cyclohexyloxy)-2H-isoquinolin-1-one (151) were dissolved in 15 mL of TFA and heated in a microwave oven at 150° C. for 2 h. Methanol was added and the reaction mixture was evaporated. The solution was taken up in 1N HCl and extracted three times with dichloromethane. The combined dichloromethane layers were extracted with 1N HCl twice and the combined HCl layers were lyophilized, the residue was taken up in water and lyophilized again to yield 1.31 g of 6-(4-methylamino-cyclohexyloxy)-2H-isoquinolin-1-one (152) as hydrochloride. Rt=0.81 min (Method B). Detected mass: 273.2 (M+H+).

Workup

customthe reaction mixture was evaporated
extractionextracted three times with dichloromethane
extractionThe combined dichloromethane layers were extracted with 1N HCl twice

Sources & evidence

ORD record: ord-1a760cc125104bf88c41901687627a6a
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796458B2

Reaction notes

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