HCID 90112155, compound → HCID 90109546, compound

HRID 1508841Notes

Reaction equation

HRID 1508841 reaction equation
[C:1]1([C:6]2[CH:11]=[C:10]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([CH2:19][C:20]([OH:22])=[O:21])=[CH:15][CH:14]=3)[CH:9]=[C:8]([C:23]([F:26])([F:25])[F:24])[N:7]=2)[CH2:5][CH2:4][CH2:3][CH:2]=1>C(O)C.[Pd]>[CH:1]1([C:6]2[CH:11]=[C:10]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([CH2:19][C:20]([OH:22])=[O:21])=[CH:15][CH:14]=3)[CH:9]=[C:8]([C:23]([F:26])([F:24])[F:25])[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 90112155HCID 90112155, compound

Product 1

HCID 90109546HCID 90109546, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-(4-((2-(cyclopent-1-en-1-yl)-6-(trifluoromethyl)pyridin-4-yl)amino)phenyl)acetic acid (0.050 g, 0.14 mmol) in ethanol (5 mL) was added 10% Pd/C (0.002 g) and the mixture was stirred under an hydrogen atmosphere at rt for 48 h. After this time, the mixture was cooled and filtered through celite with ethanol washing. The filtrate was dried over sodium sulfate, filtered, and concentrated. The residue was purified by column chromatography (silica, hexane/ethyl acetate) to afford the title compound (0.021 g, 43%) as a light brown solid. MW=364.36. 1H NMR (DMSO-d6, 500 MHz) δ 9.09 (s, 1H), 7.27 (d, J=8.0 Hz, 2H), 7.16 (d, J=8.0 Hz, 2H), 7.03 (s, 1H), 6.93 (s, 1H), 3.54 (s, 2H), 3.10-3.01 (m, 1H), 2.01-1.89 (m, 2H), 1.81-1.57 (m, 6H), 1.24 (s, 1H); APCI MS m/z 365 [M+H]+.

Workup

  1. temperatureAfter this time, the mixture was cooled
  2. filtrationfiltered through celite with ethanol washing
  3. dry with materialThe filtrate was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (silica, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-94068618e26949fba9bf3eca0cad3b1c
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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