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Ethylene glycol dioxane → 2-(1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazol-3-yl)isonicotinamide

HRID 2174282
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HRID 2174282 반응식
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[N:12]=[C:11]([C:13]3[S:14][CH:15]=[CH:16][N:17]=3)[N:10]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])[N:9]=2)[CH:3]=1.[Cu][C:27]#[N:28].C(O)C[OH:31].O1CCOCC1>[Cl-].[Na+].O>[F:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][N:10]1[C:11]([C:13]2[S:14][CH:15]=[CH:16][N:17]=2)=[N:12][C:8]([C:4]2[CH:3]=[C:2]([CH:7]=[CH:6][N:5]=2)[C:27]([NH2:28])=[O:31])=[N:9]1
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참가 물질

5

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HCID 22419261Ethylene glycol dioxaneHCID 690942852-(3-(4-bromopyridin-2-yl)-1-(2-fluorobenzyl)-1H-1,2,4-triazol-5-yl)thiazoleHCID 178418546HCID 178418546, 화합물

생성물 1

HCID 690929042-(1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazol-3-yl)isonicotinamide수율 11%

시약·촉매·용매 1

HCID 57417360Sodium chloride; water
용매

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온도
100 °C

실험 절차

To a stirring suspension of 2-(3-(4-bromopyridin-2-yl)-1-(2-fluorobenzyl)-1H-1,2,4-triazol-5-yl)thiazole (I-36, 1 equiv) in ethylene glycol-dioxane (approx. 4:1) in a sealed tube was added copper(I) cyanide (3 equiv). The resultant reaction mixture was heated at 100° C. for 24 hr and then cooled to room temperature, treated with brine and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, concentrated and purified using SiO2 chromatography (ethyl acetate/hexanes) to afford 2-(1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazol-3-yl)isonicotinamide as a solid in 11% yield.

후처리

  1. customThe resultant reaction mixture
  2. temperaturecooled to room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated
  6. custompurified

출처 및 근거

ORD 기록
ord-462b5e32433448ea8a0ccb44da82d892
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09061030B2

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