HCID 58097144, compound → HCID 178519566, compound

HRID 1897956Notes

Reaction equation

HRID 1897956 reaction equation
C([N:5]1[C:9]([NH:10][C:11]2[N:16]=[C:15]([CH2:17][C:18]3([C:37]4[O:41][C:40](=[O:42])[NH:39][N:38]=4)[CH2:23][CH2:22][N:21]([C:24](=[O:36])[C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[C:26]=4[F:35])[CH2:20][CH2:19]3)[CH:14]=[CH:13][CH:12]=2)=[CH:8][CH:7]=[N:6]1)(C)(C)C>C(O)=O>[F:35][C:26]1[C:27]([C:31]([F:34])([F:33])[F:32])=[CH:28][CH:29]=[CH:30][C:25]=1[C:24]([N:21]1[CH2:22][CH2:23][C:18]([C:37]2[O:41][C:40](=[O:42])[NH:39][N:38]=2)([CH2:17][C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([NH:10][C:9]3[CH:8]=[CH:7][NH:6][N:5]=3)[N:16]=2)[CH2:19][CH2:20]1)=[O:36]

Participants

3

Reactant 1

HCID 58097144HCID 58097144, compound

Product 1

HCID 178519566HCID 178519566, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
90 °C

Procedure

71 mg of 5-(4-((6-((1-tert-butyl-1H-pyrazol-5-yl)amino)pyridin-2-yl)methyl)-1-(2-fluoro-3-(trifluoromethyl)benzoyl)piperidin-4-yl)-1,3,4-oxadiazol-2(3H)-one was dissolved in 1.5 ml of formic acid at room temperature, followed by stirring the reaction mixture at 90° C. overnight. The reaction mixture was cooled to room temperature, and concentrated in vacuo. The resulting residue was basified with saturated aqueous sodium bicarbonate solution, and extracted with ethyl acetate. The ethyl acetate solution was dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated in vacuo. The resulting residue was purified by a preparative thin-layer chromatography (Kieselgel™ 60F254, Art5744 (Merck), chloroform/methanol=10/1) to give the title compound as a pale yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. extractionextracted with ethyl acetate
  4. dry with materialThe ethyl acetate solution was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customThe resulting residue was purified by a preparative thin-layer chromatography (Kieselgel™ 60F254, Art5744 (Merck), chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-691a113badb14f50988cb4b919ae5e51
Source dataset
uspto-grants-2013_08
Patent number
US08519136B2

Reaction notes

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