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Hydrochloric Acid → 2-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)-8-((cis)-3-fluoropiperidin-4-yloxy)quinoline

HRID 2035646
ノート
印刷プレビュー

反応式

HRID 2035646 の反応式
[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([O:20][C@H:21]4[CH2:26][CH2:25][N:24](C(OCC5C=CC=CC=5)=O)[CH2:23][C@H:22]4[F:37])[CH:14]=[CH:15][CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.Cl.C([O-])(O)=O.[Na+]>O1CCOCC1>[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([O:20][C@H:21]4[CH2:26][CH2:25][NH:24][CH2:23][C@H:22]4[F:37])[CH:14]=[CH:15][CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12
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

5

反応物 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 131731018(cis)-Benzyl 4-(2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)-3-fluoropiperidine-1-carboxylate

生成物 1

HCID 672309412-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)-8-((cis)-3-fluoropiperidin-4-yloxy)quinoline

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

Enantiomer 1 of (cis)-benzyl 4-(2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)-3-fluoropiperidine-1-carboxylate (0.185 g, 0.372 mmol) was dissolved in dioxane (4.6 mL) and treated with 6 M hydrogen chloride (4.65 mL, 27.9 mmol) and the reaction mixture was heated at 100° C. for 2 hours. The reaction was cooled and carefully neutralized with solid NaHCO3. The resulting aqueous layer (pH 8-9) was extracted four times with methylene chloride and the resulting organic layers were combined and dried over Na2SO4 then concentrated in vacuo. The residue was chromatographed on SiO2 eluting with a gradient of 6% NH4OH in MeOH)/methylene chloride. The desired material was isolated as a colorless film (22 mg). MS APCI (+) m/z 364.1 (M+1) detected.

後処理

  1. temperatureThe reaction was cooled
  2. extractionThe resulting aqueous layer (pH 8-9) was extracted four times with methylene chloride
  3. dry with materialdried over Na2SO4
  4. concentrationthen concentrated in vacuo
  5. customThe residue was chromatographed on SiO2 eluting with a gradient of 6% NH4OH in MeOH)/methylene chloride

出典と根拠

ORDレコード
ord-469842aa1a804cac901224d242a5dc96
出典データセット
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08575145B2

反応ノート

読み込み中…

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