Acryloyl chloride → HCID 46916413、化合物

HRID 2045931ノート

反応式

HRID 2045931 の反応式
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[C:11]1[CH:12]=[C:13]([NH2:17])[CH:14]=[CH:15][CH:16]=1.C(N(C(C)C)CC)(C)C.[C:27](Cl)(=[O:30])[CH:28]=[CH2:29]>C1COCC1.C(OCC)(=O)C>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[C:11]1[CH:12]=[C:13]([NH:17][C:27](=[O:30])[CH:28]=[CH2:29])[CH:14]=[CH:15][CH:16]=1

参加物

6

反応物 3

HCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 8072643-(2-Quinoxalinyl)aniline

生成物 1

HCID 46916413HCID 46916413、化合物収率 87.6%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of (3-quinoxalin-2-ylphenyl)amine (100 mg, 0.452 mmol) and diisopropylethylamine (DIEA, 90 μL, 0.542 mmol) in THF (5 mL), acryloyl chloride (41 μL, 0.497 mmol) was added at room temperature and the reaction mixture was stirred for 24 hrs. Upon diluted with ethyl acetate (25 mL), the organic phase was washed with water (25 mL), dried over MgSO4, filtered and the solvent evaporated in vacuo to afford N-(3-(quinoxalin-2-yl)phenyl)acrylamide (109 mg, 87% yield). LCMS calculated for C17H13N3O (M+H): 276.31. found 276.17. 1H-NMR (DMSO-d6, 400 Mhz) δH: 10.49 (1H, br.), 9.52 (1H, s), 8.60 (1H, m), 8.13-8.16 (2H, m), 8.05-8.08 (1H, m), 7.80-7.95 (3H, m), 7.55-7.60 (1H, m), 6.48-6.58 (1H, dd, J=10 Hz and 16.5 Hz), 6.32 (1H, d, J=16.5 Hz), 5.80 (1H, d, J=10 Hz).

後処理

  1. washthe organic phase was washed with water (25 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customthe solvent evaporated in vacuo

出典と根拠

ORDレコード
ord-b313f9f3dc7847fdab40d9c53aed920a
出典データセット
uspto-grants-2013_11
特許番号
US08592415B2

反応ノート

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