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

HRID 2174290노트

반응식

HRID 2174290 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-46375e3f141d4441ac624cdb2dea3297
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09061030B2

반응 노트

불러오는 중…