1-Fluoro-4-(methylsulphonyl)benzene → [1,2,4]Triazolo[1,5-a]pyridin-2-amine

HRID 472516ノート

反応式

HRID 472516 の反応式
[NH2:1][C:2]1[N:11]=[C:5]2[C:6](O)=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.FC1C=CC(S(C)(=O)=O)=CC=1.CC(C)([O-])C.[K+]>CN(C)C(=O)C>[N:11]1[C:2]([NH2:1])=[N:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

参加物

5

反応物 3

HCID 679941-Fluoro-4-(methylsulphonyl)benzeneHCID 23665647Potassium tert-butoxideHCID 67481450HCID 67481450、化合物

生成物 1

HCID 584054[1,2,4]Triazolo[1,5-a]pyridin-2-amine

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
130 °C

実験手順

A well stirred mixture of 2-amino-[1,2,4]triazolo[1,5-a]pyridine-8-ol (0.300 g, 2.00 mmol), 1-fluoro-4-methanesulfonyl-benzene (0.418 g, 2.40 mmol), N,N-dimethylacetamide (2 mL) and potassium tert-butoxide (0.448 g, 4.00 mmol) was heated at 130° C. for 18 h under an argon atmosphere. The reaction mixture was evaporated in vacuo and partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution. The aqueous phase was extracted twice with dichloromethane and the combined organic layers were washed with brine, dried over sodium sulfate, filtered, and evaporated in vacuo to furnish a crude product. The crude product was purified by preparative Gilson HPLC method to yield a pure product, which was triturated from a mixture of dichloromethane, methanol, ether and hexane. 8-(4-Methanesulfonyl-phenoxy)-[1,2,4-triazolo[1,5-a]pyridin-2-ylamine was isolated as a white solid (125 mg, 20%). MP=245-247° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 8.53 (d, J=6.56 Hz, 1H), 7.87 (d, J=8.77 Hz, 2H), 7.36 (d, J=7.73 Hz, 1H), 7.15 (d, J=8.76 Hz, 2H), 6.92 (t, J=7.28 Hz, 1H), 6.13 (s, 1H), 3.19 (s, 3H). MS=305 (MH)+.

後処理

  1. customThe reaction mixture was evaporated in vacuo
  2. custompartitioned between dichloromethane and saturated aqueous sodium bicarbonate solution
  3. extractionThe aqueous phase was extracted twice with dichloromethane
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto furnish a crude product
  9. customThe crude product was purified by preparative Gilson HPLC method
  10. customto yield a pure product, which
  11. customwas triturated from a mixture of dichloromethane, methanol, ether and hexane

出典と根拠

ORDレコード
ord-71c331633c1648f7bf48034a61817c22
出典データセット
uspto-grants-2014_01
特許番号
US08633173B2

反応ノート

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