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Sodium Hydroxide → 6-(1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazol-3-yl)pyridin-2-amine

HRID 2174281
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HRID 2174281 반응식
Br[C:2]1[N:7]=[C:6]([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:5]=[CH:4][CH:3]=1.[OH-].[NH4+:27].[OH-].[Na+]>C(O)CO.O1CCOCC1.[Cu-]=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:6]2[N:7]=[C:2]([NH2:27])[CH:3]=[CH:4][CH:5]=2)=[N:9]1
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참가 물질

6

반응물 3

HCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 867132002-(3-(6-bromopyridin-2-yl)-1-(2-fluorobenzyl)-1H-1,2,4-triazol-5-yl)thiazole

생성물 1

HCID 690942396-(1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazol-3-yl)pyridin-2-amine수율 69%

시약·촉매·용매 2

HCID 178419072HCID 178419072, 화합물촉매
HCID 22419261
Ethylene glycol dioxane
용매

실험 절차

To a suspension of 2-(3-(6-bromopyridin-2-yl)-1-(2-fluorobenzyl)-1H-1,2,4-triazol-5-yl)thiazole (I-19) and copper(I) oxide (0.2 eq) in ethylene glycol-dioxane (4:1) in a sealed tube was added ammonium hydroxide solution (˜29% in water, ˜30 eq). The resultant mixture was warmed to 100° C. and stirred at that temperature for 24 h. The reaction solution was cooled to rt, poured into 1N NaOH solution and then extracted with EtOAc. The organic phases were dried over Na2SO4, filtered and conc. The crude product was purified using SiO2 chromatography and an appropriate gradient (EtOAc/hexanes) to give 6-(1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazol-3-yl)pyridin-2-amine as a white solid (I-14, 69% yield).

후처리

  1. extractionextracted with EtOAc
  2. dry with materialThe organic phases were dried over Na2SO4
  3. filtrationfiltered
  4. customconc. The crude product was purified

출처 및 근거

ORD 기록
ord-eeea2319a5d741a691d8263b50267465
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09061030B2

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