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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
ノート
印刷プレビュー

反応式

HRID 595547 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

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

生成物 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-carboxamide収率 52%

試薬・触媒・溶媒 1

HCID 176
Acetic Acid
溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-60bf5092727841d096d0a5ff05b338aa
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09242998B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート