1-Methylpiperazine → N-(4-(8-(4-Methylpiperazin-1-yl)-6-oxo-5,6-dihydrobenzo[c][1,8]naphthyridin-1-ylamino)phenyl)benzamide

HRID 1029234Notes

Reaction equation

Cl[C:2]1[CH:3]=[CH:4][C:5]2[C:14]3[C:9](=[N:10][CH:11]=[CH:12][C:13]=3[NH:15][C:16]3[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:30])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:18][CH:17]=3)[NH:8][C:7](=[O:31])[C:6]=2[CH:32]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[CH3:67][N:68]1[CH2:73][CH2:72][NH:71][CH2:70][CH2:69]1>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:67][N:68]1[CH2:73][CH2:72][N:71]([C:2]2[CH:3]=[CH:4][C:5]3[C:14]4[C:9](=[N:10][CH:11]=[CH:12][C:13]=4[NH:15][C:16]4[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:30])[C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)=[CH:18][CH:17]=4)[NH:8][C:7](=[O:31])[C:6]=3[CH:32]=2)[CH2:70][CH2:69]1

Participants

Conditions

Temperature: 100 °C

Procedure

275 (44 mg, 0.10 mmol), Pd(OAc)2 (6 mg 0.02 mmol), X-Phos (19 mg, 0.04 mmol), and 1-methylpiperazine (0.02 mL, 0.20 mmol) were suspended in dioxane (3 mL), and stirred overnight at 100° C. for overnight. The crude reaction mixture purified via HP-LC to provide 276. LC-MS (M+H=505, obsd.=505).

Workup

customThe crude reaction mixture
custompurified via HP-LC

Sources & evidence

ORD record: ord-13ce798e32a5413994324b67321d710e
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735584B2

Reaction notes

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