HCID 58097106, compound → HCID 178468504, compound

HRID 1897951Notes

Reaction equation

HRID 1897951 reaction equation
C([N:5]1[C:9]([NH:10][C:11]2[N:16]=[C:15]([CH2:17][C:18]3([C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH2:23][CH2:22][N:21]([C:24](=[O:33])[C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[C:26]=4[F:32])[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>[Cl:31][C:27]1[C:26]([F:32])=[C:25]([CH:30]=[CH:29][CH:28]=1)[C:24]([N:21]1[CH2:20][CH2:19][C:18]([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)([C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH2:23][CH2:22]1)=[O:33]

Participants

3

Reactant 1

HCID 58097106HCID 58097106, compound

Product 1

HCID 178468504HCID 178468504, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
100 °C

Procedure

207 mg of ethyl 4-((6-((1-tert-butyl-1H-pyrazol-5-yl)amino)pyridin-2-yl)methyl)-1-(3-chloro-2-fluorobenzoyl)piperidine-4-carboxylate was dissolved in 3 ml of formic acid at room temperature, followed by stirring the reaction mixture at 100° C. for 8 hours. 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 resulting ethyl acetate solution was dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated in vacuo. The resulting residue was purified by a silica gel column chromatography (eluent: chloroform to chloroform/methanol=10/1) to give the title compound as a colorless oil.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. extractionextracted with ethyl acetate
  4. dry with materialThe resulting 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 silica gel column chromatography (eluent: chloroform to chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-c9287748fda84006ab63b4d778380e5d
Source dataset
uspto-grants-2013_08
Patent number
US08519136B2

Reaction notes

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