Sodium Bicarbonate → 3-Tert-butyl-7-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine

HRID 2047645ノート

反応式

HRID 2047645 の反応式
CC(C)([O-])C.[K+].[C:7]([C:11]1[N:15]2[CH2:16][CH2:17][CH:18]([C:20]([O:22]CC)=O)[CH2:19][C:14]2=[N:13][N:12]=1)([CH3:10])([CH3:9])[CH3:8].[F:25][C:26]1[CH:35]=[CH:34][C:29]([C:30](=[N:32]O)[NH2:31])=[CH:28][CH:27]=1.C(=O)(O)[O-].[Na+]>O1CCCC1.[Cl-].[Na+].O>[C:7]([C:11]1[N:15]2[CH2:16][CH2:17][CH:18]([C:20]3[O:22][N:32]=[C:30]([C:29]4[CH:34]=[CH:35][C:26]([F:25])=[CH:27][CH:28]=4)[N:31]=3)[CH2:19][C:14]2=[N:13][N:12]=1)([CH3:8])([CH3:9])[CH3:10]

参加物

7

反応物 4

HCID 516892Sodium BicarbonateHCID 5930004-Fluoro-n-hydroxybenzimidamideHCID 23665647Potassium tert-butoxideHCID 67300535Ethyl 3-t-butyl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-7-carboxylate

生成物 1

HCID 673002453-Tert-butyl-7-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine収率 53.4%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 57417360Sodium chloride; water溶媒

実験手順

Add dropwise potassium tert-butoxide 1M in tetrahydrofuran (2.08 Kg, 2.08 mol) to a solution of ethyl 3-tert-butyl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-7-carboxylate (455 g, 1.81 mol) and 4-fluorobenzamidoxime (320 g, 2.08 mol) in tetrahydrofuran (11 L) at room temperature. Stir the reaction mixture for 16 hours. Pour the mixture over a solution of saturated sodium bicarbonate (6 L) and add brine (3×2 L). Separate phases and extract aqueous phase with ethyl acetate (3×1 L). Combine organics, dry over magnesium sulfate, filter, and concentrate to dryness under reduced pressure. Purify the resulting residue by silica gel chromatography eluting with ethyl acetate to ethyl acetate:methanol (9:1) to provide the title compound as a white solid (330 g). Mass spectrum (m/z): 342 (M+1).

後処理

  1. extractionSeparate phases and extract aqueous phase with ethyl acetate (3×1 L)
  2. dry with materialCombine organics, dry over magnesium sulfate
  3. filtrationfilter
  4. concentrationconcentrate to dryness under reduced pressure
  5. customPurify the resulting residue by silica gel chromatography
  6. washeluting with ethyl acetate to ethyl acetate:methanol (9:1)

出典と根拠

ORDレコード
ord-48bc10895bab46198b3f8df157671d23
出典データセット
uspto-grants-2013_11
特許番号
US08592590B2

反応ノート

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