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Citric Acid → 4-Amino-5-cyano-2-fluoro-6-methylbiphenyl-3-yl cyclopentenecarboxylate

HRID 17506
Notes
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Reaction equation

HRID 17506 reaction equation
[NH2:1][C:2]1[C:9]([OH:10])=[C:8]([F:11])[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:6]([CH3:18])[C:3]=1[C:4]#[N:5].C(N(CC)CC)C.[C:26]1([C:31](Cl)=[O:32])[CH2:30][CH2:29][CH2:28][CH:27]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(#N)C>[C:26]1([C:31]([O:10][C:9]2[C:8]([F:11])=[C:7]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:6]([CH3:18])=[C:3]([C:4]#[N:5])[C:2]=2[NH2:1])=[O:32])[CH2:30][CH2:29][CH2:28][CH:27]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8471TriethylamineHCID 11332481Cyclopent-1-ene-1-carbonyl chlorideHCID 860974464-Amino-3-cyano-6-fluoro-5-hydroxy-2-methylbiphenyl

Product 1

HCID 866308604-Amino-5-cyano-2-fluoro-6-methylbiphenyl-3-yl cyclopentenecarboxylateYield 77%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

Under nitrogen atmosphere, 2-amino-5-phenyl-4-fluoro-3-hydroxy-6-methylbenzonitrile (I-41) (200 mg, 0.83 mmol) was dissolved in acetonitrile (10 ml), and cooled to 0° C. Triethylamine (195 μl, 1.4 mmol) and cyclopentenecarbonyl chloride (162 mg, 1.24 mmol) were dropwise added to the solution, followed by stirring at room temperature for 1 hour. 10% citric acid was added to the reaction liquid, and the solvent was evaporated away under reduced pressure. Ethyl acetate was added to the resulting residue, followed by washing with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated away under reduced pressure. The resulting residue was subjected to preparative silica gel column chromatography, and the eluate with ethyl acetate/hexane (1:3, v/v) gave the entitled compound (180 mg, 77%) as a white solid.

Workup

  1. customthe solvent was evaporated away under reduced pressure
  2. additionEthyl acetate was added to the resulting residue
  3. washby washing with saturated brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated away under reduced pressure

Sources & evidence

ORD record
ord-aff968b72d364d3fad2fd0fb7189e419
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07737166B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes