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

HRID 589067ノート

反応式

HRID 589067 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e340495f717745b8b31b421cec5e96f8
出典データセット
uspto-grants-2016_01
特許番号
US09227985B2

反応ノート

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