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

HRID 589135ノート

反応式

HRID 589135 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8782d4cde2ce498ab54724fb7674bc83
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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