Methanol → 6-((1S,3S)-3-Amino-cyclopentyloxy)-2H-isoquinolin-1-one

HRID 402536Notes

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][C@H:19]4[CH2:23][CH2:22][C@H:21]([NH2:24])[CH2:20]4)[CH:14]=3)[C:9]2=[O:25])=CC=1.CO>C(O)(C(F)(F)F)=O>[NH2:24][C@H:21]1[CH2:22][CH2:23][C@H:19]([O:18][C:13]2[CH:14]=[C:15]3[C:10](=[CH:11][CH:12]=2)[C:9](=[O:25])[NH:8][CH:17]=[CH:16]3)[CH2:20]1

Participants

Conditions

Temperature: 150 °C

Procedure

125 mg (0.34 mmol) of 2-(4-methoxy-benzyl)-6-((1S,3S)-3-amino-cyclopentyloxy)-2H-isoquinolin-1-one (39) were dissolved in 1 mL of TFA and heated in a microwave oven at 150° C. for 3 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 dissolved in water and lyophilized again to yield 42 mg of 6-((1S,3S)-3-amino-cyclopentyloxy)-2H-isoquinolin-1-one (43) as hydrochloride. Rt=0.86 min (Method E). Detected mass: 245.1 (M+H+).

Workup

customthe reaction mixture was evaporated
extractionextracted three times with dichloromethane
extractionThe combined dichloromethane layers were extracted with 1N HCl twice
dissolutionThe residue was dissolved in water

Sources & evidence

ORD record: ord-b116c9eba4fe43db893bd5fa317c0e57
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08742116B2

Reaction notes

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