Benzamide, N-(4-aminophenyl)- → 1-(4-tert-Butyl-phenylamino)-5H-benzo[c][1,8]naphthyridin-6-one

HRID 1029109

반응식

HRID 1029109 반응식
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[C:6](=[O:12])[NH:7]2.[NH2:17][C:18]1[CH:32]=[CH:31]C(NC(=O)C2C=CC=CC=2)=[CH:20][CH:19]=1.[CH:33]1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.[CH3:67][C:68]([CH3:71])([O-])[CH3:69].[Na+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:68]([C:71]1[CH:31]=[CH:32][C:18]([NH:17][C:2]2[CH:11]=[CH:10][N:9]=[C:8]3[C:3]=2[C:4]2[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=2[C:6](=[O:12])[NH:7]3)=[CH:19][CH:20]=1)([CH3:33])([CH3:69])[CH3:67]

참가 물질

7

반응물 4

HCID 87196Benzamide, N-(4-aminophenyl)-HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23676156Sodium t-butoxideHCID 581680081-Chlorobenzo[C][1,8]naphthyridin-6(5H)-one

생성물 1

HCID 581682761-(4-tert-Butyl-phenylamino)-5H-benzo[c][1,8]naphthyridin-6-one수율 320.3%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

1-Chloro-5H-benzo[c][1,8]naphthyridin-6-one (50 mg, 0.22 mmol), 4′-aminobenzanilide (92 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 solution was concentrated, diluted with MeOH/2M HCl/ether, and filtered. The crude product was purified directly via prep-LC-MS. The purified product was converted to the HCl salt via dissolving in MeOH, addition of 2M HCl/ether, and concentration on the Genevac to provide 119 (22 mg, 23% yield) as a dark solid. LC-MS (M+H=407, obsd.=407). 1H NMR (400 MHz, d6-DMSO): δ 10.33 (s, 1H), 9.52 (s, 1H), 8.78 (d, 1H), 8.36 (d, 1H), 8.09 (d, 1H), 7.96 (d, 2H), 7.81 (d, 2H), 7.55 (m, 5H), 7.26 (d, 2H), 6.93 (d, 1H).

후처리

  1. concentrationThe reaction solution was concentrated
  2. additiondiluted with MeOH/2M HCl/ether
  3. filtrationfiltered
  4. customThe crude product was purified directly via prep-LC-MS
  5. dissolutionvia dissolving in MeOH
  6. additionaddition of 2M HCl/ether, and concentration on the Genevac

출처 및 근거

ORD 기록
ord-6a53f8a5f1194d7fb3ac17f5f3ec0c9c
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08735584B2

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