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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
ノート
印刷プレビュー

反応式

HRID 550851 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b468b67dcc6247a8b1b4697e28d92f49
出典データセット
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07947692B2

反応ノート

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