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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 2174271
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인쇄 미리보기

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HRID 2174271 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
참가 물질실험 절차후처리출처 및 근거반응 노트

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-amine

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 (e.g., about 0.2 eq) in ethylene glycol-dioxane (e.g., about 4:1) in a sealed tube is added ammonium hydroxide solution (e.g., ˜29% in water, ˜30 eq). The resultant mixture is warmed to about 100° C. and stirred at that temperature for about 24 h. The reaction solution is cooled to room temperature, poured into 1N NaOH solution and then extracted with EtOAc. The organic phases are dried, e.g., over Na2SO4 or MgSO4, filtered and concentrated. The crude product is 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 (I-14) as a solid.

후처리

  1. extractionextracted with EtOAc
  2. customThe organic phases are dried
  3. filtratione.g., over Na2SO4 or MgSO4, filtered
  4. concentrationconcentrated
  5. customThe crude product is purified

출처 및 근거

ORD 기록
ord-cf582c8eb95c4516b35ee2b1a63d8aff
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09061030B2

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