tert-butyl (3-(3-(4-cyanophenyl)-7-nitro-1-oxo-3,4-dihydroisoquinolin-2(1H)-yl)propyl)carbamate → tert-butyl (3-(7-amino-3-(4-cyanophenyl)-1-oxo-3,4-dihydroisoquinolin-2(1H)-yl)propyl)carbamate

HRID 2039769Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:18][C:17]3[C:12](=[CH:13][C:14]([N+:19]([O-])=O)=[CH:15][CH:16]=3)[C:11](=[O:22])[N:10]2[CH2:23][CH2:24][CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:5][CH:4]=1)#[N:2].[H][H]>CO.[Pd]>[NH2:19][C:14]1[CH:13]=[C:12]2[C:17]([CH2:18][CH:9]([C:6]3[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)[N:10]([CH2:23][CH2:24][CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[C:11]2=[O:22])=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of Intermediate 1 (350 mg, 0.78 mmol) in 20 mL of MeOH was added 10% Pd/C (40 mg). A balloon filled with hydrogen gas was attached, and the reaction was stirred at 25° C. for 12 hrs. The mixture was filtered through Celite pad and the solvent was evaporated. The residue was purified by medium pressure liquid chromatography on silica gel using ethyl acetate:hexane (8:2) to yield Intermediate 13 as a yellow solid.

Workup

filtrationThe mixture was filtered through Celite pad
customthe solvent was evaporated
customThe residue was purified by medium pressure liquid chromatography on silica gel

Sources & evidence

ORD record: ord-4c7d9f4a89c846ff81a321c5b891e2c2
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580817B2

Reaction notes

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