3-Methoxybenzylamine → HCID 69812279, compound

HRID 1029085Notes

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:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22][NH2:23].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:26]1[CH:19]=[CH:20][C:21]([CH2:22][NH:23][C:2]2[CH:3]=[C:4]3[C:9](=[N:10][CH:11]=2)[NH:8][C:7](=[O:12])[C:6]2[CH:13]=[CH:14][CH:15]=[CH:16][C:5]3=2)=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 100 °C

Procedure

2-Chloro-5H-benzo[c][1,8]naphthyridin-6-one (50 mg, 0.22 mmol), 3-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 37 (10 mg, 12% yield) as a yellow solid. LC-MS (M+H=332, obsd.=332). 1H NMR (400 MHz, d6-DMSO): δ 11.68 (s, 1H), 8.38 (d, 1H), 8.29 (dd, 1H), 8.05 (d, 1H), 7.91 (d, 1H), 7.84 (dt, 1H), 7.63 (t, 1H), 7.25 (t, 1H), 7.05 (m, 2H), 6.80 (d, 1H), 3.78 (s, 2H), 3.71 (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-66c865763b34400ba7ad37c7f1d88458
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735584B2

Reaction notes

Loading…