4-Methoxybenzylamine → HCID 58168026, compound

HRID 1029084Notes

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.COC1C=CC(C[NH2:24])=CC=1.C1(P(C2CCCCC2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[C:40]2[C:45](C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.[Na].[O-:62][CH2:63]CCC>O1CCOCC1.CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:63][O:62][C:38]1[CH:37]=[CH:36][C:35]([CH2:40][CH2:45][NH:24][C:15]2[CH:14]=[CH:13][C:6]3[C:7](=[O:12])[NH:8][C:9]4[C:4]([C:5]=3[CH:16]=2)=[CH:3][CH:2]=[CH:11][N:10]=4)=[CH:34][CH:39]=1

Participants

Conditions

Temperature: 100 °C

Procedure

2-Chloro-5H-benzo[c][1,8]naphthyridin-6-one (50 mg, 0.22 mmol), 4-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 ted-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 36 (10 mg, 14% yield) as a yellow solid. LC-MS (M+H=332, obsd.=332). 1H NMR (400 MHz, d6-DMSO): δ 8.38 (d, 1H), 8.29 (d, 1H), 8.10 (d, 1H), 7.88 (d, 1H), 7.39 (m, 3H), 6.99 (m, 2H), 6.89 (d, 1H), 3.75 (s, 3H), 3.71 (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-c9b14bfffc714a469586bfe28c06d340
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735584B2

Reaction notes

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