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 1511116노트

반응식

HRID 1511116 반응식
[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>[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

참가 물질

6

반응물 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

생성물 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-amine수율 56.5%

시약·촉매·용매 1

HCID 962Water용매

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온도
40 °C

실험 절차

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 g, 0.764 mmol) was added 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-dioxolan-4-yl)-1,2,4-thiadiazol-5-amine (0.233 g, 56.5% yield) as yellow solid.

후처리

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

출처 및 근거

ORD 기록
ord-354a1f521dec4f9eb641f8a38abbb2c3
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08212045B2

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