Pyridine → (S)-N-(5-(pyridin-2-ylthio)-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)pyridin-2-yl)-3-(2,2,5,5-tetramethyl-1,3-dioxolan-4-yl)-1,2,4-thiadiazol-5-amine

HRID 534096ノート

反応式

HRID 534096 の反応式
[CH3:1][C:2]1([CH3:17])[O:6][C@@H:5]([C:7](Cl)=[N:8]OS(C)(=O)=O)[C:4]([CH3:16])([CH3:15])[O:3]1.[S-:18][C:19]#[N:20].[Na+].N1C=CC=CC=1.[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[S:34][C:35]1[CH:36]=[C:37]([O:42][C:43]2[C:44]([CH3:50])=[N:45][N:46]([CH3:49])[C:47]=2[CH3:48])[C:38]([NH2:41])=[N:39][CH:40]=1>O.C(#N)C>[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[S:34][C:35]1[CH:36]=[C:37]([O:42][C:43]2[C:44]([CH3:50])=[N:45][N:46]([CH3:49])[C:47]=2[CH3:48])[C:38]([NH:41][C:19]2[S:18][N:8]=[C:7]([C@H:5]3[C:4]([CH3:15])([CH3:16])[O:3][C:2]([CH3:1])([CH3:17])[O:6]3)[N:20]=2)=[N:39][CH:40]=1

参加物

7

反応物 4

HCID 1049PyridineHCID 516871Sodium thiocyanateHCID 674864745-(Pyridin-2-ylthio)-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)pyridin-2-amineHCID 86644154(R)-2,2,5,5-tetramethyl-N-(methylsulfonyloxy)-1,3-dioxolane-4-carbimidoyl chloride

生成物 1

HCID 68473453(S)-N-(5-(pyridin-2-ylthio)-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)pyridin-2-yl)-3-(2,2,5,5-tetramethyl-1,3-dioxolan-4-yl)-1,2,4-thiadiazol-5-amine収率 56.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
40 °C

実験手順

A flask was charged with (R)-2,2,5,5-tetramethyl-N-(methylsulfonyloxy)-1,3-dioxolane-4-carbimidoyl chloride (0.371 g, 1.30 mmol), sodium thiocyanate (0.0929 g, 1.15 mmol), pyridine (0.278 ml, 3.44 mmol), and acetonitrile (25 mL) and the reaction was heated to 40° C. for 30 minutes. 5-(Pyridin-2-ylthio)-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)pyridin-2-amine (0.250 g, 0.764 mmol) was added and the reaction was stirred at 70° C. overnight. Water was added and the reaction was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified over silica gel (50 to 100% ethyl acetate in hexanes) to afford (S)-N-(5-(pyridin-2-ylthio)-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)pyridin-2-yl)-3-(2,2,5,5-tetramethyl-1,3-dioxolane-4-yl)-1,2,4-thiadiazol-5-amine (0.233 g, 56.5% yield) as yellow solid.

後処理

  1. extractionthe reaction was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified over silica gel (50 to 100% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-1f12ad4cf6ef44a5ae52c04ce30cac0b
出典データセット
uspto-grants-2014_10
特許番号
US08853409B2

反応ノート

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