O-(Diphenylphosphinyl)hydroxylamine → 2-amino-4-morpholinophthalazin-1(2H)-one

HRID 535478

반응식

HRID 535478 반응식
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[NH:9][N:8]=2)[CH2:3][CH2:2]1.CC([O-])(C)C.[K+].C1(P(O[NH2:39])(C2C=CC=CC=2)=O)C=CC=CC=1>C1COCC1.CCOC(C)=O>[NH2:39][N:9]1[N:8]=[C:7]([N:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]1=[O:17]

참가 물질

6

반응물 3

HCID 10955453O-(Diphenylphosphinyl)hydroxylamineHCID 126895281(2H)-Phthalazinone, 4-(4-morpholinyl)-HCID 23665647Potassium tert-butoxide

생성물 1

HCID 709761042-amino-4-morpholinophthalazin-1(2H)-one수율 39.5%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of the product from Example 1A (0.300 g, 1.30 mmol) in THF (3.5 mL) was added a 1 M solution of potassium 2-methylpropan-2-olate in THF (1.7 mL, 1.7 mmol). The mix was stirred at room temperature for 90 minutes, and O-(diphenylphosphoryl)hydroxylamine (0.395 g, 1.70 mmol) was added and stirred overnight. The mixture was diluted with EtOAc, washed with 0.5N NaOH and water, concentrated, and chromatographed (40% EtOAc/DCM) to give 126.4 mg of product as a white solid: 1H NMR (300 MHz, DMSO-d6) δ 8.31-8.25 (m, 1H), 8.03-7.98 (m, 1H), 7.94-7.80 (m, 2H), 6.20 (s, 2H), 3.87-3.78 (m, 4H), 3.15-3.07 (m, 4H).

후처리

  1. stirringstirred overnight
  2. washwashed with 0.5N NaOH and water
  3. concentrationconcentrated
  4. customchromatographed (40% EtOAc/DCM)

출처 및 근거

ORD 기록
ord-99f319cc28084ba4a31bd398a7df37c7
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859549B2

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