Diisopropylethylamine → N-methyl-2-oxo-4-pyridin-2-yl-1,2,4,5-tetrahydroimidazo[1,5,4-de][1,4]benzoxazine-4-carboxamide

HRID 589067노트

반응식

HRID 589067 반응식
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[NH2:13][C:14]1[C:19]2[NH:20][C:21]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=3)([C:24]([NH:26][CH3:27])=[O:25])[CH2:22][O:23][C:18]=2[CH:17]=[CH:16][CH:15]=1.C(N(CC)C(C)C)(C)C>O1CCCC1>[CH3:27][NH:26][C:24]([C:21]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)[N:20]2[C:2](=[O:4])[NH:13][C:14]3=[CH:15][CH:16]=[CH:17][C:18](=[C:19]23)[O:23][CH2:22]1)=[O:25]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 904090745-amino-N-methyl-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazine-3-carboxamide

생성물 1

HCID 90409674N-methyl-2-oxo-4-pyridin-2-yl-1,2,4,5-tetrahydroimidazo[1,5,4-de][1,4]benzoxazine-4-carboxamide수율 249.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Triphosgene (10 mg, 0.04 mmol) was added to a solution of 5-amino-N-methyl-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazine-3-carboxamide (30 mg, 0.1 mmol) in tetrahydrofuran (3 mL) and N,N-diisopropylethylamine (40 μL, 0.2 mmol) at room temperature and was stirred for 1 h. The reaction mixture was then partitioned between ethyl acetate and water, and the organic layer was washed with brine, dried over magnesium sulfate, and concentrated to give crude N-methyl-2-oxo-4-pyridin-2-yl-1,2,4,5-tetrahydroimidazo[1,5,4-de][1,4]benzoxazine-4-carboxamide as a semisolid (0.031 g, 100%). LCMS calculated for C16H15N4O3 (M+H)+: m/z=311.1. found: 311.1.

후처리

  1. customThe reaction mixture was then partitioned between ethyl acetate and water
  2. washthe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e340495f717745b8b31b421cec5e96f8
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227985B2

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