2-Methoxybenzylamine → HCID 69811484, compound

HRID 1029086Notes

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.CO[C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21][NH2:22].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C[C:62](C)([O-:64])C.[Na+]>O1CCOCC1.CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:62][O:64][C:24]1[CH:23]=[C:20]([CH:19]=[CH:26][CH:25]=1)[CH2:21][NH:22][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), 2-methoxy-benzylamine (59 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 38 (6 mg, 8% yield) as a yellow solid. LC-MS (M+H=332, obsd.=332). 1H NMR (400 MHz, d6-DMSO): δ 11.68 (s, 1H), 8.37 (d, 1H), 8.31 (d, 1H), 8.05 (d, 1H), 7.91 (d, 1H), 7.85 (t, 1H), 7.64 (t, 1H), 7.36 (m, 1H), 7.24 (m, 1H), 7.02 (m, 1H), 6.89 (t, 1H), 4.32 (s, 2H), 3.88 (s, 3H).

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-51b1628780e041308d9ec95ad92b9b62
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735584B2

Reaction notes

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