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Sodium Bicarbonate → (rac)-7-(4-Cyanophenyl)-5-methyl-2-thiophen-2-yl-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitrile

HRID 2200924
ノート
印刷プレビュー

反応式

HRID 2200924 の反応式
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]=[C:9]([NH2:11])[NH:8][N:7]=1.[C:12]([C:14]([C:24](=O)[CH3:25])=[CH:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1)#[N:13].C(=O)(O)[O-].[Na+]>CN(C=O)C>[C:20]([C:19]1[CH:22]=[CH:23][C:16]([CH:15]2[N:8]3[N:7]=[C:6]([C:2]4[S:1][CH:5]=[CH:4][CH:3]=4)[N:10]=[C:9]3[NH:11][C:24]([CH3:25])=[C:14]2[C:12]#[N:13])=[CH:17][CH:18]=1)#[N:21]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 666280804-(2-Cyano-3-oxobut-1-en-1-yl)benzonitrileHCID 178508309HCID 178508309、化合物

生成物 1

HCID 136355665(rac)-7-(4-Cyanophenyl)-5-methyl-2-thiophen-2-yl-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitrile

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
55 °C

実験手順

Under an atmosphere of argon, 3-(2-thienyl)-1H-1,2,4-triazole-5-amine (318 mg, 1.9 mmol) and 4-(2-cyano-3-oxobut-1-en-1-yl)benzonitrile (300 mg, 1.5 mmol, 0.8 eq.) were dissolved in DMF (3 ml), and solid sodium bicarbonate (803 mg, 9.6 mmol, 5 eq.) was added. The mixture was stirred at 55° C. for 12 h. The mixture was then filtered, and the DMF from the filtrate was distilled off under reduced pressure. The residue was purified by preparative HPLC (Kromasil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA). The product was obtained as a solid (73.7 mg, 91% pure, 12% of theory).

後処理

  1. filtrationThe mixture was then filtered
  2. distillationthe DMF from the filtrate was distilled off under reduced pressure
  3. customThe residue was purified by preparative HPLC (Kromasil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA)
  4. customThe product was obtained as a solid (73.7 mg, 91% pure, 12% of theory)

出典と根拠

ORDレコード
ord-e99aa215b0df4f369b5e02997bff9bc5
出典データセット
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09359362B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート