Acetic Acid Mixture with Hydrobromic Acid → HCID 90341045, 화합물

HRID 595560노트

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HRID 595560 반응식
[F:1][C:2]1[C:3]2[CH:4]=[C:5]3[C:14]4[N:15]=[C:16]([C:19]5[C:20]([N:40]([CH3:45])[S:41]([CH3:44])(=[O:43])=[O:42])=[CH:21][C:22]6[O:26][C:25]([C:27]7[CH:28]=[N:29][C:30]([O:33]C)=[CH:31][CH:32]=7)=[C:24]([C:35]([NH:37][CH3:38])=[O:36])[C:23]=6[CH:39]=5)[CH:17]=[CH:18][C:13]=4[O:12][CH2:11][N:6]3[C:7]=2[CH:8]=[CH:9][CH:10]=1.Br.CC(O)=O>CC(O)=O>[F:1][C:2]1[C:3]2[CH:4]=[C:5]3[C:14]4[N:15]=[C:16]([C:19]5[C:20]([N:40]([CH3:45])[S:41]([CH3:44])(=[O:43])=[O:42])=[CH:21][C:22]6[O:26][C:25]([C:27]7[CH:32]=[CH:31][C:30](=[O:33])[NH:29][CH:28]=7)=[C:24]([C:35]([NH:37][CH3:38])=[O:36])[C:23]=6[CH:39]=5)[CH:17]=[CH:18][C:13]=4[O:12][CH2:11][N:6]3[C:7]=2[CH:8]=[CH:9][CH:10]=1

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HCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 778453345-(11-fluoro-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indol-2-yl)-2-(6-methoxypyridin-3-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

생성물 1

HCID 90341045HCID 90341045, 화합물수율 50%

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
80 °C

실험 절차

To a solution of 5-(11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)-2-(6-methoxypyridin-3-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (40 mg, 0.64 mmol) in HOAc (4 mL) was added HBr—HOAc (4 ml) at 0° C. Then the mixture was stirred at 80° C. for 2 hours. After the solvent was removed by vacuum, the residue was washed with Na2CO3 (a.q.), extracted with DCM, dried over Na2SO4, filtrated and concentrated in vacuo. The residue was purified by prep-HPLC to give the product 5-(11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)-N-methyl-6-(N-methylmethylsulfonamido)-2-(6-oxo-1,6-dihydropyridin-3-yl)benzofuran-3-carboxamide (20 mg, yield: 50%). 1H-NMR (MeOD, 400 MHz) δ 8.33 (s, 1H), 7.96 (q, J=9.6 Hz, 1H), 7.84 (s, 1H), 7.88 (s, 1H), 7.55 (d, J=9.6 Hz, 2H), 7.28 (d, J=9.6 Hz, 1H), 7.15˜7.21 (m, 2H), 6.87 (q, J=9.6 Hz, 1H), 6.53 (t, J=9.6 Hz, 1H), 6.06 (s, 2H), 3.31 (s, 3H), 2.95 (d, J=9.6 Hz, 3H), 2.85 (s, 3H). MS (M+H)+: 614.

후처리

  1. customAfter the solvent was removed by vacuum
  2. washthe residue was washed with Na2CO3 (a.q.)
  3. extractionextracted with DCM
  4. dry with materialdried over Na2SO4
  5. filtrationfiltrated
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by prep-HPLC

출처 및 근거

ORD 기록
ord-15ddf713935e487194e55bb7d76a8387
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242998B2

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