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Ammonium Hydroxide → 2-(1-(2-fluorobenzyl)-5-(oxazol-4-yl)-1H-1,2,4-triazol-3-yl)pyridin-4-amine

HRID 2174284
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HRID 2174284 반응식
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[N:12]=[C:11]([C:13]3[N:14]=[CH:15][O:16][CH: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.[OH-].[NH4+:27]>C(O)CO.O1CCOCC1.[Cl-].[Na+].O.[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[N:14]=[CH:15][O:16][CH:17]=2)=[N:12][C:8]([C:4]2[CH:3]=[C:2]([NH2:27])[CH:7]=[CH:6][N:5]=2)=[N:9]1
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참가 물질

6

반응물 2

HCID 14923Ammonium HydroxideHCID 690943024-(3-(4-bromopyridin-2-yl)-1-(2-fluorobenzyl)-1H-1,2,4-triazol-5-yl)oxazole

생성물 1

HCID 690937872-(1-(2-fluorobenzyl)-5-(oxazol-4-yl)-1H-1,2,4-triazol-3-yl)pyridin-4-amine수율 41.2%

시약·촉매·용매 3

HCID 178419072HCID 178419072, 화합물촉매HCID 22419261Ethylene glycol dioxane용매
HCID 57417360Sodium chloride; water용매

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온도
100 °C

실험 절차

To a stirring suspension of 4-(3-(4-bromopyridin-2-yl)-1-(2-fluorobenzyl)-1H-1,2,4-triazol-5-yl)oxazole (I-54, 1 eq) and copper(I) oxide (0.2 eq) in ethylene glycol-dioxane (approx. 4:1) in a sealed tube was added ammonium hydroxide (30 eq). The resultant reaction mixture was heated at 100° C. for 12 hr. The reaction was cooled to room temperature and treated with brine and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, concentrated and purified using SiO2 chromatography (DCM/CAN/MeOH) to afford 2-(1-(2-fluorobenzyl)-5-(oxazol-4-yl)-1H-1,2,4-triazol-3-yl)pyridin-4-amine in 41.2% yield.

후처리

  1. customThe resultant reaction mixture
  2. temperatureThe reaction was cooled 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-df5893ef685d445eb27c6fbe07cf12d7
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09061030B2

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