N-bromobutanimide → N-[(7-bromo-2-oxo-4-pyridin-2-yl-1,2,4,5-tetrahydroimidazo[1,5,4-de][1,4]benzoxazin-4-yl)methyl]acetamide

HRID 589073노트

반응식

HRID 589073 반응식
[Br:1]N1C(=O)CCC1=O.[O:9]=[C:10]1[N:18]2[C:19]([CH2:28][NH:29][C:30](=[O:32])[CH3:31])([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[CH2:20][O:21][C:16]3=[C:17]2[C:12](=[CH:13][CH:14]=[CH:15]3)[NH:11]1>C(#N)C.C(O)(=O)C>[Br:1][C:15]1[C:16]2[O:21][CH2:20][C:19]([CH2:28][NH:29][C:30](=[O:32])[CH3:31])([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[N:18]3[C:10](=[O:9])[NH:11][C:12]([C:17]=23)=[CH:13][CH:14]=1

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 90409826N-[(2-oxo-4-pyridin-2-yl-1,2,4,5-tetrahydroimidazo[1,5,4-de][1,4]benzoxazin-4-yl)methyl]acetamide

생성물 1

HCID 90408820N-[(7-bromo-2-oxo-4-pyridin-2-yl-1,2,4,5-tetrahydroimidazo[1,5,4-de][1,4]benzoxazin-4-yl)methyl]acetamide수율 60%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6342Acetonitrile용매

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온도
0 °C

실험 절차

N-Bromosuccinimide (40 mg, 0.2 mmol) was added to a mixture of N-[(2-oxo-4-pyridin-2-yl-1,2,4,5-tetrahydroimidazo[1,5,4-de][1,4]benzoxazin-4-yl)methyl]acetamide in acetonitrile (5 mL) and acetic acid (3 mL), and cooled to 0° C. The reaction was stirred for 1 h, concentrated to remove residual acetic acid, and partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated to give crude N-[(7-bromo-2-oxo-4-pyridin-2-yl-1,2,4,5-tetrahydroimidazo[1,5,4-de][1,4]benzoxazin-4-yl)methyl]acetamide (0.040 g. 60%). LCMS calculated for C17H16BrN4O3 (M+H)+: m/z=403.1, 405.1. found: 402.9, 405.0.

후처리

  1. concentrationconcentrated
  2. customto remove residual acetic acid
  3. custompartitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-48638ae5045c4c2a8228d5dfa6641f2a
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227985B2

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