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

HRID 595547
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HRID 595547 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:32]=[CH:31][N:30]=[C:29]([O:33]C)[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.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][NH:30][C:29](=[O:33])[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 778451135-(11-fluoro-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indol-2-yl)-2-(2-methoxypyridin-4-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

생성물 1

HCID 903410595-(11-fluoro-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indol-2-yl)-N-methyl-6-(N-methylmethylsulfonamido)-2-(2-oxo-1,2-dihydropyridin-4-yl)benzofuran-3-carboxamide수율 52%

시약·촉매·용매 1

HCID 176
Acetic Acid
용매

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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-(2-methoxypyridin-4-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (30 mg, 0.05 mmol) in HOAc (1 mL) was added HBr—HOAc (1 mL) at 0° C. Then the mixture was stirred at 80° C. for 2 hours. The solvent was removed by vacuum and NaHCO3 (a.q.) was added. The mixture was extracted with DCM, and the organic phase was dried over Na2SO4. After concentrated in vacuo, the residue was purified by prep-HPLC to give the product of 5-(11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)-N-methyl-6-(N-methylmethylsulfonamido)-2-(2-oxo-1,2-dihydropyridin-4-yl)benzofuran-3-carboxamide (15 mg, yield: 52%). 1H-NMR (DMSO-d6, 400 MHz) δ 8.73˜8.75 (m, 1H), 8.11 (s, 1H), 7.85 (s, 1H), 7.73 (q, J=8.8 Hz, 1H), 7.59˜7.62 (m, 2H), 7.51˜7.61 (m, 2H), 7.25˜7.27 (m, 1H), 7.11 (s, 1H), 6.88˜6.96 (m, 1H), 6.65 (d, J=2.8 Hz, 1H), 6.27 (s, 2H), 3.31 (s, 3H), 2.97 (s, 3H), 2.85 (d, J=4.0 Hz, 3H). MS (M+H)+: 614.

후처리

  1. customThe solvent was removed by vacuum and NaHCO3 (a.q.)
  2. additionwas added
  3. extractionThe mixture was extracted with DCM
  4. dry with materialthe organic phase was dried over Na2SO4
  5. concentrationAfter concentrated in vacuo
  6. customthe residue was purified by prep-HPLC

출처 및 근거

ORD 기록
ord-60bf5092727841d096d0a5ff05b338aa
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09242998B2

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