Methanol → HCID 178484836, compound

HRID 1913141Notes

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-91a52b4baefe47eab60cfd81f1596ef0
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609691B2

Reaction notes

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