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Ammonium thiocyanate → [1-(7-Methoxy-thiazolo[5,4-b]pyridin-2-ylcarbamoyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester

HRID 550851
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HRID 550851 반응식
[C:1]([O:5][C:6](=[O:16])[NH:7][CH:8]1[CH2:12][CH2:11][N:10]([C:13](Cl)=[O:14])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[S-:17][C:18]#[N:19].[NH4+].[NH2:21][C:22]1[C:23](Cl)=[N:24][CH:25]=[CH:26][C:27]=1[O:28][CH3:29]>CC(C)=O>[C:1]([O:5][C:6](=[O:16])[NH:7][CH:8]1[CH2:12][CH2:11][N:10]([C:13](=[O:14])[NH:19][C:18]2[S:17][C:23]3[C:22]([N:21]=2)=[C:27]([O:28][CH3:29])[CH:26]=[CH:25][N:24]=3)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]
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참가 물질

5

반응물 3

HCID 15666Ammonium thiocyanateHCID 157900532-Chloro-4-methoxypyridin-3-amineHCID 76655536(1-Chlorocarbonyl-pyrrolidin-3-yl)carbamic acid tert-butyl ester

생성물 1

HCID 72489371[1-(7-Methoxy-thiazolo[5,4-b]pyridin-2-ylcarbamoyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester수율 15%

시약·촉매·용매 1

HCID 180Acetone
용매

실험 절차

A magnetically stirred mixture of (1-Chlorocarbonyl-pyrrolidin-3-yl)carbamic acid tert-butyl ester (820 mg, 3.30 mmol) in acetone (15 mL) under a nitrogen atmosphere at 25 C was treated with ammonium thiocyanate (240 mg, 3.15 mmol). The reaction mixture was stirred at reflux for 30 min. At this time, the reaction was treated with 3-amino-2-chloro-4 methoxypyridine (440 mg, 2.78 mmol). The reaction mixture was refluxed overnight. At this time, the reaction was concentrated in vacuo, poured into water and extracted with ethyl acetate. The organics were washed with a 2N aqueous hydrochloric acid solution and a saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 98:2 methylene chloride/methanol) afforded [1-(7-Methoxy-thiazolo[5,4-b]pyridin-2-ylcarbamoyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester (160 mg, 15%) as a light yellow solid. LRMS for C17H23N5O4S (M+H)+ at m/z=393. The NMR spectrum obtained on the sample is compatible with its structure.

후처리

  1. temperatureat reflux for 30 min
  2. temperatureThe reaction mixture was refluxed overnight
  3. concentrationAt this time, the reaction was concentrated in vacuo
  4. additionpoured into water
  5. extractionextracted with ethyl acetate
  6. washThe organics were washed with a 2N aqueous hydrochloric acid solution
  7. dry with materiala saturated aqueous sodium chloride solution, dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-b468b67dcc6247a8b1b4697e28d92f49
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07947692B2

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