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

HRID 595548
ノート
印刷プレビュー

反応式

HRID 595548 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:39]([CH3:44])[S:40]([CH3:43])(=[O:42])=[O:41])=[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:34]([NH:36][CH3:37])=[O:35])[C:23]=6[CH:38]=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.[C:45]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[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:39]([CH3:44])[S:40]([CH3:43])(=[O:42])=[O:41])=[CH:21][C:22]6[O:26][C:25]([C:27]7[CH:32]=[CH:31][N:30]([CH3:45])[C:29](=[O:33])[CH:28]=7)=[C:24]([C:34]([NH:36][CH3:37])=[O:35])[C:23]=6[CH:38]=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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 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

生成物 1

HCID 778454145-(11-fluoro-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indol-2-yl)-N-methyl-2-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide収率 53.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a suspension 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 (20 mg, 0.03 mmol) and K2CO3 (10 mg, 0.06 mmol) in DMF (1 mL) was added CH3I (5 mg, 0.03 mol) at 0° C. under N2, and then the mixture was stirred for 12 hours at room temperature. After being concentrated in vacuo, the resulting residue was suspended in H2O and extracted with DCM. The combined organic layer was washed with H2O and dried over Na2SO4. After concentration, 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-2-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (10 mg, yield: 49%). 1H-NMR (DMSO-d6, 400 MHz) δ 8.7˜28.74 (m, 1H), 8.10 (s, 1H), 7.84˜7.86 (m, 2H), 7.70˜7.72 (m, 1H), 7.59˜7.62 (m, 1H), 7.50˜7.53 (m, 1H), 7.24˜7.28 (m, 1H), 7.23 (s, 1H), 6.96˜7.09 (m, 2H), 6.67˜6.91 (m, 1H), 6.27 (s, 2H), 3.48 (s, 3H), 3.31 (s, 3H), 2.97 (s, 3H), 2.85 (d, J=4.4 Hz, 3H). MS (M+H)+: 628.

後処理

  1. concentrationAfter being concentrated in vacuo
  2. extractionextracted with DCM
  3. washThe combined organic layer was washed with H2O
  4. dry with materialdried over Na2SO4
  5. concentrationAfter concentration
  6. customthe residue was purified by prep-HPLC

出典と根拠

ORDレコード
ord-5f159ba73e444c9999ff803c5e6d6ef7
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実験手順後処理出典と根拠反応ノート