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 1509301ノート

反応式

HRID 1509301 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

実験手順

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).

後処理

  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%)

出典と根拠

ORDレコード
ord-75fa7c5eccc24c41b28851281d2c880a
出典データセット
uspto-grants-2015_12
特許番号
US09221838B2

反応ノート

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