Pyridine → (R)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-N-(3-(2-methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-yl)-1,2,4-thiadiazol-5-amine

HRID 1523680ノート

反応式

HRID 1523680 の反応式
[CH3:1][C:2]1([CH3:15])[O:6][C@H:5]([C:7](Cl)=[N:8]OS(C)(=O)=O)[CH2:4][O:3]1.[S-:16][C:17]#[N:18].[Na+].N1C=CC=CC=1.[CH3:26][C:27]1[C:32]([O:33][C:34]2[C:35]([NH2:47])=[N:36][CH:37]=[C:38]([S:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=3)[CH:39]=2)=[CH:31][CH:30]=[CH:29][N:28]=1>O.C(OCC)(=O)C>[CH3:15][C:2]1([CH3:1])[O:6][C@H:5]([C:7]2[N:18]=[C:17]([NH:47][C:35]3[C:34]([O:33][C:32]4[C:27]([CH3:26])=[N:28][CH:29]=[CH:30][CH:31]=4)=[CH:39][C:38]([S:40][C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=4)=[CH:37][N:36]=3)[S:16][N:8]=2)[CH2:4][O:3]1

参加物

7

反応物 4

HCID 1049PyridineHCID 516871Sodium thiocyanateHCID 674857913-(2-Methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-amineHCID 86644161(S)-2,2-dimethyl-N-(methylsulfonyloxy)-1,3-dioxolane-4-carbimidoyl chloride

生成物 1

HCID 68477969(R)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-N-(3-(2-methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-yl)-1,2,4-thiadiazol-5-amine収率 77%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
40 °C

実験手順

A flask was charged with (S)-2,2-dimethyl-N-(methylsulfonyloxy)-1,3-dioxolane-4-carbimidoyl chloride (4.5 g, 18 mmol), sodium thiocyanate (1.3 g, 15 mmol), pyridine (3.8 ml, 46 mmol), and ethyl acetate (200 mL). The reaction was stirred and heated at 40° C. for 45 minutes. 3-(2-Methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-amine (3.2 g, 10 mmol) was added and the reaction was stirred at 70° C. overnight. Water was added and the reaction was extracted with ethyl acetate, dried over sodium sulfate, filtered and concentrated. The residue was purified over silica gel (25 to 100% ethyl acetate in hexanes) to afford (R)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-N-(3-(2-methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyri din-2-yl)-1,2,4-thiadiazol-5-amine (3.8 g, 7.7 mmol, 75% yield).

後処理

  1. stirringthe reaction was stirred at 70° C. overnight
  2. extractionthe reaction was extracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified over silica gel (25 to 100% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-0f03a58a97bf4d49ba4a4d3f47028e2f
出典データセット
uspto-grants-2015_07
特許番号
US09079890B2

反応ノート

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