Trifluoroacetic acid → N-(3-(isoxazol-3-ylcarbamoyl)phenyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamide

HRID 2383446Notes

Reaction equation

[O:1]1[CH:5]=[CH:4][C:3]([NH:6][C:7]([C:9]2[CH:10]=[C:11]([NH:15][C:16]([N:18]3[CH2:27][C:26]4[CH:25]=[N:24][C:23]5[N:28](CC6C=CC(OC)=CC=6)[N:29]=[CH:30][C:22]=5[C:21]=4[CH2:20][CH2:19]3)=[O:17])[CH:12]=[CH:13][CH:14]=2)=[O:8])=[N:2]1.FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[O:1]1[CH:5]=[CH:4][C:3]([NH:6][C:7]([C:9]2[CH:10]=[C:11]([NH:15][C:16]([N:18]3[CH2:27][C:26]4[CH:25]=[N:24][C:23]5[NH:28][N:29]=[CH:30][C:22]=5[C:21]=4[CH2:20][CH2:19]3)=[O:17])[CH:12]=[CH:13][CH:14]=2)=[O:8])=[N:2]1

Participants

Conditions

Temperature: 65 °C

Procedure

Step 2 To the crude N-(3-(isoxazol-3-ylcarbamoyl)phenyl)-3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamide obtained above was added trifluoroacetic acid (1 mL). The reaction mixture was shaken at 65° C. for 16 hours. On completion of the reaction, toluene (1 mL) was added and solvent removed under reduced pressure. The crude product was purified reverse phase HPLC to give the desired product, N-(3-(isoxazol-3-ylcarbamoyl)phenyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamide. LCMS [M+H]: 404.

Workup

additionwas added
customsolvent removed under reduced pressure
customThe crude product was purified reverse phase HPLC

Sources & evidence

ORD record: ord-d94b077466a0489d85f0a876c4be5fc9
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263610B2

Reaction notes

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