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

HRID 589072노트

반응식

HRID 589072 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]([CH2:30][NH:31][C:32](=[O:34])[CH3:33])([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)[CH2:22][O:23][C:18]=2[CH:17]=[CH:16][CH:15]=1.C(N(CC)C(C)C)(C)C>O1CCCC1>[O:4]=[C:2]1[N:20]2[C:21]([CH2:30][NH:31][C:32](=[O:34])[CH3:33])([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)[CH2:22][O:23][C:18]3=[C:19]2[C:14](=[CH:15][CH:16]=[CH:17]3)[NH:13]1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 90409013N-[(5-amino-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazin-3-yl)methyl]acetamide

생성물 1

HCID 90409826N-[(2-oxo-4-pyridin-2-yl-1,2,4,5-tetrahydroimidazo[1,5,4-de][1,4]benzoxazin-4-yl)methyl]acetamide수율 176.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Triphosgene (20 mg, 0.07 mmol) was added to a mixture of N-[(5-amino-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazin-3-yl)methyl]acetamide (50 mg, 0.2 mmol), tetrahydrofuran (5 mL) and N,N-diisopropylethylamine (60 μL) at room temperature. The reaction was stirred for 1 h then partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated to give crude N-[(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. 70%). LCMS calculated for C17H17N4O3 (M+H)+: m/z=325.1. found: 325.1.

후처리

  1. customthen partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-732396bb6a14459aa731063c356cd4f9
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227985B2

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