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Water → tert-butyl (1S,3R)-3-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentylcarbamate

HRID 1854378
ノート
印刷プレビュー

反応式

HRID 1854378 の反応式
S([N:11]1[C:15]2=[N:16][CH:17]=[C:18]([NH:20][NH:21][C:22]([C@@H:24]3[CH2:28][CH2:27][C@H:26]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:25]3)=O)[N:19]=[C:14]2[CH:13]=[CH:12]1)(C1C=CC(C)=CC=1)(=O)=O.O=S(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+].O>O1CCOCC1.CCOC(C)=O>[C:22]1([C@@H:24]2[CH2:28][CH2:27][C@H:26]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:25]2)[N:19]2[C:14]3[CH:13]=[CH:12][NH:11][C:15]=3[N:16]=[CH:17][C:18]2=[N:20][N:21]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 58009789tert-butyl (1S,3R)-3-(2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazinecarbonyl)cyclopentylcarbamate

生成物 1

HCID 136198944tert-butyl (1S,3R)-3-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentylcarbamate収率 90.9%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

To a solution of tert-butyl (1S,3R)-3-(2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazinecarbonyl)cyclopentylcarbamate (4.73 g, 9.19 mmol) in 1,4-dioxane (50 mL) was added TEA (5.10 mL, 36.8 mmol) and SOCl2 (1.34 mL, 18.4 mmol). The reaction mixture was heated at about 80° C. After about 1.5 h, saturated aqueous Na2CO3 (100 mL) was added and heating was resumed at about 80° C. for about 6 h. The reaction mixture was cooled to ambient temperature for about 3 days and then heated at about 80° C. for about 16 h. Water and EtOAc (100 mL each) were added and the layers were separated. The aqueous layer was then extracted with additional EtOAc (2×100 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude solid was triturated with petroleum ether (b.p. 30-60° C.; 30 mL) and collected by vacuum filtration, while washing with additional petroleum ether (b.p. 30-60° C.; 20 mL), to give tert-butyl (1S,3R)-3-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentylcarbamate as a light brown solid (2.86 g, 86%): LC/MS (Table 2, Method a) Rt=1.75 min; MS m/z: 343 (M+H)+.

後処理

  1. temperatureheating
  2. waitwas resumed at about 80° C. for about 6 h
  3. temperatureThe reaction mixture was cooled to ambient temperature for about 3 days
  4. temperatureheated at about 80° C. for about 16 h
  5. customthe layers were separated
  6. extractionThe aqueous layer was then extracted with additional EtOAc (2×100 mL)
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over anhydrous Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe crude solid was triturated with petroleum ether (b.p. 30-60° C.; 30 mL)
  12. filtrationcollected by vacuum filtration
  13. washwhile washing with additional petroleum ether (b.p. 30-60° C.; 20 mL)

出典と根拠

ORDレコード
ord-380864dbb5a340918b0c223704ec3ac3
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08962629B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート