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

HRID 589067Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 589067
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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 90409674N-methyl-2-oxo-4-pyridin-2-yl-1,2,4,5-tetrahydroimidazo[1,5,4-de][1,4]benzoxazine-4-carboxamideAusbeute 249,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-e340495f717745b8b31b421cec5e96f8
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09227985B2

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