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

HRID 2035650
ノート
印刷プレビュー

反応式

HRID 2035650 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+].[Na+].[Cl-]>O1CCOCC1.O>[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

7

反応物 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 131731020(trans)-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 672301232-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)-8-((trans)-3-fluoropiperidin-4-yloxy)quinoline

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

Non-racemic (trans)-benzyl 4-(2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)-3-fluoropiperidine-1-carboxylate (0.304 g, 0.611 mmol) was dissolved in dioxane (7.6 mL) and treated with 6 M hydrogen chloride (7.64 mL, 45.8 mmol), and the reaction mixture was heated at 100° C. for 15 hours. The reaction was cooled and carefully neutralized with solid NaHCO3. Additional water was added to dissolve the resulting NaCl as the neutralization proceeded. The resulting aqueous layer (pH 8-9) was extracted with methylene chloride and the combined organic layers were dried over Na2SO4 and concentrated in vacuo. The crude product was chromatographed on SiO2 eluting with a gradient of 2% NH4OH in isopropanol/methylene chloride. The desired product was isolated as a white foam (62.6 mg). MS APCI (+) m/z 364.2 (M+1) detected.

後処理

  1. temperatureThe reaction was cooled
  2. extractionThe resulting aqueous layer (pH 8-9) was extracted with methylene chloride
  3. dry with materialthe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was chromatographed on SiO2 eluting with a gradient of 2% NH4OH in isopropanol/methylene chloride

出典と根拠

ORDレコード
ord-9cdbfbebd9514701a28c1d081981cf19
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…

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