Ethanol → HCID 178467496、化合物

HRID 541350ノート

反応式

HRID 541350 の反応式
[NH2:1][C:2]1[O:6][C:5]([C:7]2[C:8]([CH:31]3[CH2:34][CH2:33][CH2:32]3)=[CH:9][C:10]([CH2:29][CH3:30])=[C:11]([CH:28]=2)[C:12]([N:14]2[CH2:19][CH2:18][CH:17]([C:20]3[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)=[O:13])=[N:4][N:3]=1.[OH-:35].[K+].[CH2:37](O)[CH3:38]>>[CH:31]1([C:8]2[C:7]([C:5]3[NH:1][C:2]([O:6][CH2:37][CH3:38])=[N:3][N:4]=3)=[CH:28][C:11]([C:12]([N:14]3[CH2:15][CH2:16][CH:17]([C:20]4[CH:27]=[CH:26][C:23]([C:24]([NH2:25])=[O:35])=[CH:22][CH:21]=4)[CH2:18][CH2:19]3)=[O:13])=[C:10]([CH2:29][CH3:30])[CH:9]=2)[CH2:32][CH2:33][CH2:34]1

参加物

4

反応物 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 682883904-(1-(5-(5-Amino-1,3,4-oxadiazol-2-yl)-4-cyclobutyl-2-ethylbenzoyl)piperidin-4-yl)benzonitrile2 回

生成物 1

HCID 178467496HCID 178467496、化合物

反応条件

温度
80 °C

実験手順

To a 10-mL sealed tube, which was purged and maintained with an inert atmosphere of nitrogen, was added a solution of 4-(1-(5-(5-amino-1,3,4-oxadiazol-2-yl)-4-cyclobutyl-2-ethylbenzoyl)piperidin-4-yl)benzonitrile (compound 215.7, 228 mg, 0.500 mmol, 1.00 equiv) in ethanol (5 mL). This was followed by the addition of potassium hydroxide (280 mg, 4.99 mmol, 10.0 equiv) in portions. The resulting solution was stirred for 5 h at 80° C. behind a blast shield. After cooling to ambient temperature, the reaction was then quenched by the addition of 15 mL of water and extracted with 2×20 mL of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. This resulted in 200 mg (80%) of 4-(1-(4-cyclobutyl-5-(5-ethoxy-4H-1,2,4-triazol-3-yl)-2-ethylbenzoyl)piperidin-4-yl)benzamide as a yellow solid.

後処理

  1. customTo a 10-mL sealed tube
  2. customwhich was purged
  3. temperaturemaintained with an inert atmosphere of nitrogen
  4. temperatureAfter cooling to ambient temperature
  5. customthe reaction was then quenched by the addition of 15 mL of water
  6. extractionextracted with 2×20 mL of ethyl acetate
  7. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThis resulted in 200 mg (80%) of 4-(1-(4-cyclobutyl-5-(5-ethoxy-4H-1,2,4-triazol-3-yl)-2-ethylbenzoyl)piperidin-4-yl)benzamide as a yellow solid

出典と根拠

ORDレコード
ord-b4858187f88d4e95ac4aaae53bff1d69
出典データセット
uspto-grants-2014_10
特許番号
US08871790B2

反応ノート

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