4-Pyridinemethanamine → HCID 58168257, compound

HRID 1029110Notes

Reaction equation

Cl[C:2]1[CH:16]=[CH:15][C:5]2[C:6](=[O:14])[NH:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[CH:12][CH:11]=[CH:10][N:9]=3.[N:17]1[CH:22]=[CH:21][C:20]([CH2:23][NH2:24])=[CH:19][CH:18]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.CC(C)([O-])C.[Na+]>O1CCOCC1.CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:17]1[CH:22]=[CH:21][C:20]([CH2:23][NH:24][C:2]2[CH:16]=[CH:15][C:5]3[C:6](=[O:14])[NH:7][C:8]4[C:13]([C:4]=3[CH:3]=2)=[CH:12][CH:11]=[CH:10][N:9]=4)=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 100 °C

Procedure

9-Chloro-5H-benzo[c][1,8]naphthyridin-6-one (50 mg, 0.22 mmol), 1-pyridin-4-ylmethanamine (47 mg, 0.43 mmol), palladium(II) acetate (2 mg, 0.01 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (10 mg, 0.02 mmol), and sodium tert-butoxide (83 mg, 0.87 mmol) were suspended in dioxane (2 mL), and stirred overnight at 100° C. The reaction mixture was diluted with MeOH, filtered through a membrane, and purified via prep-LC-MS to provide 124 (10 mg, 15% yield) as a tan solid. LC-MS (M+H=303, obsd.=303). 1H NMR (400 MHz, d6-DMSO): δ 11.50 (s, 1H), 8.52 (m, 3H), 8.41 (d, 1H), 8.01 (dd, 1H), 7.42 (d, 2H), 7.35 (m, 2H), 7.24 (m, 1H), 6.95 (d, 1H), 4.58 (d, 2H).

Workup

filtrationfiltered through a membrane
custompurified via prep-LC-MS

Sources & evidence

ORD record: ord-b348bea270ca4dcda8a2969031a566af
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735584B2

Reaction notes

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