Acryloyl chloride → HCID 46916413, 화합물

HRID 2045931노트

반응식

HRID 2045931 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 46916413HCID 46916413, 화합물수율 87.6%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-b313f9f3dc7847fdab40d9c53aed920a
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08592415B2

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