Triethylamine → 7-Bromo-9-fluoro-4-pyridin-3-yl-4,5-dihydroimidazo[1,5,4-de][1,4]benzoxazin-2(1H)-one

HRID 589135노트

반응식

HRID 589135 반응식
C(N(CC)CC)C.[Br:8][C:9]1[CH:10]=[C:11]([F:26])[C:12]([NH2:25])=[C:13]2[C:18]=1[O:17][CH2:16][CH:15]([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)[NH:14]2.Cl[C:28](Cl)([O:30]C(=O)OC(Cl)(Cl)Cl)Cl>C1COCC1.O>[Br:8][C:9]1[C:18]2[O:17][CH2:16][CH:15]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[N:14]3[C:28](=[O:30])[NH:25][C:12]([C:13]=23)=[C:11]([F:26])[CH:10]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 904097398-Bromo-6-fluoro-3-pyridin-3-yl-3,4-dihydro-2H-1,4-benzoxazin-5-amine

생성물 1

HCID 904103367-Bromo-9-fluoro-4-pyridin-3-yl-4,5-dihydroimidazo[1,5,4-de][1,4]benzoxazin-2(1H)-one

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Triethylamine (140 μL, 1.0 mmol) was added to a solution of 8-bromo-6-fluoro-3-pyridin-3-yl-3,4-dihydro-2H-1,4-benzoxazin-5-amine (160 mg, 0.50 mmol)) in THF (6.0 mL), followed by addition of triphosgene (60 mg, 0.2 mmol), and the mixture was subsequently stirred at room temperature for 10 min. The mixture was diluted with water and extracted with ethyl acetate. The organic extracts were washed with brine and concentrated. Purification on silica gel eluting ethyl acetate in hexanes afforded the title compound. LCMS calc. for C14H10BrFN3O2 (M+H)+: m/z=350.0. found: 350.0.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic extracts were washed with brine
  3. concentrationconcentrated
  4. customPurification on silica gel
  5. washeluting ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-8782d4cde2ce498ab54724fb7674bc83
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227985B2

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