4-Toluenesulfonyl chloride → 6-Bromo-2-(5-(1,1,1-trifluoro-2-(triisopropylsilyloxy)propan-2-yl)-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)pyridin-3-amine

HRID 574210ノート

反応式

HRID 574210 の反応式
[NH2:1][C:2]1[C:3]([C:13]([NH:15][NH:16][C:17](=O)[C:18]([CH3:34])([O:23][Si:24]([CH:31]([CH3:33])[CH3:32])([CH:28]([CH3:30])[CH3:29])[CH:25]([CH3:27])[CH3:26])[C:19]([F:22])([F:21])[F:20])=[O:14])=[N:4][C:5]([Br:12])=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.S(Cl)(C1C=CC(C)=CC=1)(=O)=O>C(Cl)Cl>[Br:12][C:5]1[N:4]=[C:3]([C:13]2[O:14][C:17]([C:18]([O:23][Si:24]([CH:25]([CH3:26])[CH3:27])([CH:28]([CH3:29])[CH3:30])[CH:31]([CH3:33])[CH3:32])([CH3:34])[C:19]([F:21])([F:22])[F:20])=[N:16][N:15]=2)[C:2]([NH2:1])=[CH:7][C:6]=1[C:8]([F:9])([F:10])[F:11]

参加物

4

反応物 2

HCID 73974-Toluenesulfonyl chlorideHCID 867295973-Amino-6-bromo-N'-(3,3,3-trifluoro-2-methyl-2-(triisopropylsilyloxy)propanoyl)-5-(trifluoromethyl)picolinohydrazide

生成物 1

HCID 867295986-Bromo-2-(5-(1,1,1-trifluoro-2-(triisopropylsilyloxy)propan-2-yl)-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)pyridin-3-amine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a cooled (0° C.) solution of 3-amino-6-bromo-N′-(3,3,3-trifluoro-2-methyl-2-(triisopropylsilyloxy) propanoyl)-5-(trifluoromethyl)picolinohydrazide (5.42 g, 9.10 mmol) in DCM (50 ml) was added TEA (3.81 ml, 27.3 mmol). The resulting solution was stirred at 0° C. for 5 minutes and treated with Tosyl chloride (5.21 g, 27.3 mmol). The mixture was allowed to warm to RT and stirred for 48 h. The reaction mixture was partitioned between DCM (100 ml) and water (100 ml), phases shaken and separated. The organic portion was washed with 1M NaOH (100 ml), 1M HCl (100 ml), water (100 ml), brine (100 ml), dried (MgSO4) (˜10 g) and concentrated in vacuo to give an orange oil. Purification of the oil by chromatography on silica eluting with 0-15% EtOAc in iso-hexane afforded the title compound; LC-MS Rt=7.41 min [M+H]+ 577/579 Method 10minLC_v003.

後処理

  1. temperatureto warm to RT
  2. stirringstirred for 48 h
  3. customThe reaction mixture was partitioned between DCM (100 ml) and water (100 ml), phases
  4. stirringshaken
  5. customseparated
  6. washThe organic portion was washed with 1M NaOH (100 ml), 1M HCl (100 ml), water (100 ml), brine (100 ml)
  7. dry with materialdried (MgSO4) (˜10 g)
  8. concentrationconcentrated in vacuo
  9. customto give an orange oil
  10. customPurification of the oil by chromatography on silica eluting with 0-15% EtOAc in iso-hexane

出典と根拠

ORDレコード
ord-e7ec9d0b9bcd48629a812171d23f356a
出典データセット
uspto-grants-2015_05
特許番号
US09034879B2

反応ノート

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