4-Fluorobenzylamine → HCID 69812440, compound

HRID 1029087Notes

Reaction equation

Cl[C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]1[CH:13]=[CH:14][CH:15]=[CH:16][C:5]2=1.F[C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH2:23])=[CH:20][CH:19]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C[C:61](C)([O-:63])C.[Na+]>O1CCOCC1.CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:61][O:63][C:24]1[CH:25]=[CH:18][CH:19]=[CH:20][C:21]=1[CH2:22][NH:23][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]1[CH:13]=[CH:14][CH:15]=[CH:16][C:5]2=1

Participants

Conditions

Temperature: 100 °C

Procedure

2-Chloro-5H-benzo[c][1,8]naphthyridin-6-one (50 mg, 0.22 mmol), 4-fluoro-benzylamine (54 mg, 0.43 mmol), palladium(II) acetate (2 mg, 0.01 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (8 mg, 0.02 mmol), and sodium tert-butoxide (63 mg, 0.65 mmol) were suspended in dioxane (2 mL), and stirred overnight at 100° C. The reaction mixture was diluted with MeOH, filtered through a filter membrane, and purified via prep-LC-MS. The recovered product was converted to the HCl salt via suspending in CH2Cl2, addition of 2 M HCl/ether, filtering the resulting precipitate, and washing with CH2Cl2 to provide 39 (5 mg, 6% yield) as a yellow solid. LC-MS (M+H=320, obsd.=320). 1H NMR (400 MHz, d6-DMSO): δ 11.65 (s, 1H), 8.38 (d, 1H), 8.29 (d, 1H), 8.04 (d, 1H), 7.88 (m, 2H), 7.64 (m, 1H), 7.49 (m, 2H), 7.14 (m, 2H), 4.42 (s, 2H).

Workup

filtrationfiltered through a filter membrane
custompurified via prep-LC-MS
additionaddition of 2 M HCl/ether
filtrationfiltering the resulting precipitate
washwashing with CH2Cl2

Sources & evidence

ORD record: ord-941f40bbecad4a939f2c7aef734da832
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735584B2

Reaction notes

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