Trifluoroacetic anhydride → 1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazole-3-carbonitrile

HRID 2174290ノート

反応式

HRID 2174290 の反応式
[F:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[C:9]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=[N:8][C:7]([C:15]([NH2:17])=O)=[N:6]1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C([O-])(O)=O.[Na+]>N1C=CC=CC=1>[F:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[C:9]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=[N:8][C:7]([C:15]#[N:17])=[N:6]1

参加物

5

反応物 3

HCID 9845Trifluoroacetic anhydrideHCID 516892Sodium BicarbonateHCID 690939441-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazole-3-carboxamide

生成物 1

HCID 690942931-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazole-3-carbonitrile収率 88%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

A solution of 1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazole-3-carboxamide (Intermediate-4, 0.86 mmol) in pyridine (3.0 mL) at 0° C. was treated with trifluoroacetic anhydride (2 equiv) dropwise over the course of 5 min. The reaction was then warmed to ambient temperature and stirred for 2 h. The reaction mixture was poured into saturated NaHCO3 solution and extracted with CH2Cl2. The organic phases were dried over MgSO4, filtered and conc. The crude product was purified using SiO2 chromatography and an appropriate solvent gradient (EtOAc/hexanes) to give 1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazole-3-carbonitrile as white solid (88% yield).

後処理

  1. extractionextracted with CH2Cl2
  2. dry with materialThe organic phases were dried over MgSO4
  3. filtrationfiltered
  4. customconc. The crude product was purified

出典と根拠

ORDレコード
ord-46375e3f141d4441ac624cdb2dea3297
出典データセット
uspto-grants-2015_06
特許番号
US09061030B2

反応ノート

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