Hydrochloric Acid → 2-(7-(2-Methoxyethoxy)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-8-(piperazin-1-yl)quinoline

HRID 1041954ノート

反応式

HRID 1041954 の反応式
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][N:9]2[C:12]([C:15]3[CH:24]=[CH:23][C:22]4[C:17](=[C:18]([N:25]5[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26]5)[CH:19]=[CH:20][CH:21]=4)[N:16]=3)=[N:13][N:14]=[C:8]2[CH:7]=1.Cl.[OH-].[Na+]>C1COCC1.CO.O1CCOCC1>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][N:9]2[C:12]([C:15]3[CH:24]=[CH:23][C:22]4[C:17](=[C:18]([N:25]5[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]5)[CH:19]=[CH:20][CH:21]=4)[N:16]=3)=[N:13][N:14]=[C:8]2[CH:7]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67234014Tert-butyl 4-(2-(7-(2-methoxyethoxy)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl)piperazine-1-carboxylate

生成物 1

HCID 461786642-(7-(2-Methoxyethoxy)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-8-(piperazin-1-yl)quinoline収率 23%

試薬・触媒・溶媒 2

HCID 312751,4-Dioxane溶媒HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

To a solution of tert-butyl 4-(2-(7-(2-methoxyethoxy)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl)piperazine-1-carboxylate (0.022 g, 0.0436 mmol) in THF/MeOH (1 mL) was added 4 M HCl (0.109 mL, 0.436 mmol) in dioxane. The reaction mixture was stirred at ambient temperature for 16 hours then neutralized with 1 M NaOH and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified via flash column chromatography (40:1 DCM/MeOH followed by 10:1 DCM/MeOH) to provide 4 mg (23%) of desired product as a yellow solid. MS APCI (+) m/z 405.4 (M+1) detected.

後処理

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified via flash column chromatography (40:1 DCM/MeOH followed by 10:1 DCM/MeOH)

出典と根拠

ORDレコード
ord-d30ef2a93b2c442c82c86dd10a82f506
出典データセット
uspto-grants-2013_10
特許番号
US08557809B2

反応ノート

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