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

HRID 339667노트

반응식

HRID 339667 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 312751,4-Dioxane용매HCID 21899815MeOH tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-9e5d562129ac47c89468a54a860691a9
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895550B2

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