Ethanol → HCID 178467496, compound

HRID 541350Notes

Reaction equation

HRID 541350 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

HCID 178467496HCID 178467496, compound

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b4858187f88d4e95ac4aaae53bff1d69
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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