2,2-Difluoroacetohydrazide → 7-bromo-1-(difluoromethyl)-8-phenyl-4H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazine

HRID 1509301노트

반응식

HRID 1509301 반응식
[Br:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][C:5]2[NH:10][C:9](=S)[CH2:8][O:7][C:6]=2[N:12]=1.[F:19][CH:20]([F:25])[C:21]([NH:23][NH2:24])=O>C1(C)C(C)=CC=CC=1>[Br:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][C:5]2[N:10]3[C:21]([CH:20]([F:25])[F:19])=[N:23][N:24]=[C:9]3[CH2:8][O:7][C:6]=2[N:12]=1

참가 물질

4

반응물 2

HCID 190657972,2-DifluoroacetohydrazideHCID 866836666-bromo-7-phenyl-1H-pyrido[2,3-b][1,4]oxazine-2(3H)-thione

생성물 1

HCID 866836677-bromo-1-(difluoromethyl)-8-phenyl-4H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazine수율 22.2%

시약·촉매·용매 1

HCID 7237O-Xylene용매

실험 절차

A mixture of 6-bromo-7-phenyl-1H-pyrido[2,3-b][1,4]oxazine-2(3H)-thione (0.21 g, 0.654 mmol) and 2,2-difluoroacetohydrazide (0.14 g, 1.3 mmol) in xylene (6 ml) was heated at 150 degree under microwave for 60 min. The reaction solution was concentrated and the residue was partitioned between ethyl acetate (10 ml) and water (10 ml). The organic phase was separated and the aqueous phase was extracted with ethyl acetate (10 ml). The combined organic phase was concentrated and purified by column (biotage 25 g) eluted with ethyl acetate/cyclohexane (0-60%) to afford product (55 mg). 1H NMR (500 MHz, CDCl3) 8.09 (s, 1H), 7.4-7.55 (m, 5H), 7.06 (t, 1H), 5.66 (s, 2H).

후처리

  1. temperaturewas heated at 150 degree under microwave for 60 min
  2. concentrationThe reaction solution was concentrated
  3. customthe residue was partitioned between ethyl acetate (10 ml) and water (10 ml)
  4. customThe organic phase was separated
  5. extractionthe aqueous phase was extracted with ethyl acetate (10 ml)
  6. concentrationThe combined organic phase was concentrated
  7. custompurified by column (biotage 25 g)
  8. washeluted with ethyl acetate/cyclohexane (0-60%)

출처 및 근거

ORD 기록
ord-75fa7c5eccc24c41b28851281d2c880a
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221838B2

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