Pyridine → 1,4-Dioxaspiro[4.5]decan-2-yl-1,2,4-thiadiazol-5-amine

HRID 533997ノート

反応式

HRID 533997 の反応式
CS(O[N:6]=[C:7](Cl)[C@H:8]1[CH2:12][O:11][C:10]2([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[O:9]1)(=O)=O.[N:19]1C=CC=CC=1.[S-:25][C:26]#[N:27].[Na+].BrC1C=C(OC2C(C)=NC=CC=2)C(N)=NC=1>C(#N)C>[O:9]1[C:10]2([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[O:11][CH2:12][CH:8]1[C:7]1[N:6]=[C:26]([NH2:27])[S:25][N:19]=1

参加物

6

反応物 4

HCID 1049PyridineHCID 516871Sodium thiocyanateHCID 674861815-Bromo-3-(2-methylpyridin-3-yloxy)pyridin-2-amineHCID 86644147(R)-N-(methylsulfonyloxy)-1,4-dioxaspiro[4.5]decane-2-carbimidoyl chloride

生成物 1

HCID 866441491,4-Dioxaspiro[4.5]decan-2-yl-1,2,4-thiadiazol-5-amine収率 50%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
40 °C

実験手順

(R)-N-(methylsulfonyloxy)-1,4-dioxaspiro[4.5]decane-2-carbimidoyl chloride (1.86 g, 6.25 mmol), pyridine (1.13 g, 14.3 mmol) and sodium thiocyanate (0.58 g, 7.14 mmol) were dissolved in acetonitrile (45 mL). The solution was heated to 40° C. for 40 minutes. 5-bromo-3-(2-methylpyridin-3-yloxy)pyridin-2-amine (1.0 g, 3.57 mmol) was added and the reaction was heated at 60° C. overnight. The solution was cooled to 0° C., filtered and the solid was dried to give (S)-N-5-bromo-3-(2-methylpyridin-3-yloxy)pyridin-2-yl)-3-(1,4-dioxaspiro[4.5]decan-2-yl)-1,2,4-thiadiazol-5-amine (0.90 g, 1.78 mmol, 50% yield) as a white solid.

後処理

  1. temperaturethe reaction was heated at 60° C. overnight
  2. temperatureThe solution was cooled to 0° C.
  3. filtrationfiltered
  4. customthe solid was dried

出典と根拠

ORDレコード
ord-1558b255c35d429d82a05b1c51d93cad
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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