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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
ノート
印刷プレビュー

反応式

HRID 2174271 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178419072HCID 178419072、化合物触媒
HCID 22419261
Ethylene glycol dioxane
溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-cf582c8eb95c4516b35ee2b1a63d8aff
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09061030B2

反応ノート

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