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 1511142노트

반응식

HRID 1511142 반응식
[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

참가 물질

7

반응물 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

생성물 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-amine수율 77%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

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온도
40 °C

실험 절차

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)pyridin-2-yl)-1,2,4-thiadiazol-5-amine (3.8 g, 7.7 mmol, 75% yield).

후처리

  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)

출처 및 근거

ORD 기록
ord-f7be8551973b447b88b5c08da3235ca5
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08212045B2

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