Triphenylphosphine → 2-(4-fluorophenyl)-N-methyl-5-(12-methyl-5,6-dihydroindolo[1,2-h][1,7]naphthyridin-2-yl)-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

HRID 595752노트

반응식

HRID 595752 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:20]=[C:19]([N:21]([CH3:26])[S:22]([CH3:25])(=[O:24])=[O:23])[C:18]([C:27]4[CH:32]=[CH:31][C:30]([CH2:33][CH2:34]O)=[C:29]([C:36]5[NH:37][C:38]6[C:43]([C:44]=5[CH3:45])=[CH:42][CH:41]=[CH:40][CH:39]=6)[N:28]=4)=[CH:17][C:11]=3[C:12]=2[C:13]([NH:15][CH3:16])=[O:14])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1.CCOC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:20]=[C:19]([N:21]([CH3:26])[S:22]([CH3:25])(=[O:23])=[O:24])[C:18]([C:27]4[CH:32]=[CH:31][C:30]5[CH2:33][CH2:34][N:37]6[C:38]7[CH:39]=[CH:40][CH:41]=[CH:42][C:43]=7[C:44]([CH3:45])=[C:36]6[C:29]=5[N:28]=4)=[CH:17][C:11]=3[C:12]=2[C:13]([NH:15][CH3:16])=[O:14])=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 903335002-(4-fluorophenyl)-5-(5-(2-hydroxyethyl)-6-(3-methyl-1H-indol-2-yl)pyridin-2-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

생성물 1

HCID 903411522-(4-fluorophenyl)-N-methyl-5-(12-methyl-5,6-dihydroindolo[1,2-h][1,7]naphthyridin-2-yl)-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of 2-(4-fluorophenyl)-5-(5-(2-hydroxyethyl)-6-(3-methyl-1H-indol-2-yl)pyridin-2-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (43 mg, 0.069 mmol) and triphenylphosphine (90 mg, 0.343 mmol) in THF (4 mL) was diisopropyl azodicarboxylate (0.067 mL, 0.343 mmol). The resultant mixture was stirred at ambient temperature for 16 h, diluted with EtOAc and washed successively with H2O (2×) and brine (1×). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography using a step gradient of 0-40-90% EtOAc/Hexanes as eluent. Further purification by silica gel column chromatography with a gradient of 0-10% EtOAc/CH2Cl2 as eluent, followed by lyophilization from CH3CN/H2O provided the title compound. 1H NMR δ (ppm) (CHCl3-d): 8.16 (1H, s), 8.07˜8.03 (2H, m), 7.70˜7.66 (3H, m), 7.47 (1H, d, J=7.77 Hz), 7.37 (1H, d, J=8.24 Hz), 7.32 (1H, D, J=7.1 Hz), 7.26˜7.22 (2H, m), 7.16 (1H, t, J=7.40 Hz), 5.95 (1H, br s), 4.34 (2H, t, J=6.37 Hz), 3.32 (3H, s), 3.28 (2H, t, J=6.4 Hz), 3.05 (3H, d, J=4.91 Hz), 2.83 (3H, s), 2.75 (3H, s). MS (M+H): 609.

후처리

  1. washwashed successively with H2O (2×) and brine (1×)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. customFurther purification by silica gel column chromatography with a gradient of 0-10% EtOAc/CH2Cl2 as eluent

출처 및 근거

ORD 기록
ord-f5c7d391e24f4035a03c0c5b4be05335
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09243002B2

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