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 574210노트

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HRID 574210 반응식
[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]

참가 물질

4

반응물 2

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

생성물 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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e7ec9d0b9bcd48629a812171d23f356a
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034879B2

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