Citric Acid → HCID 86630879, compound

HRID 17561Notes

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.[CH:26]1([C:31](Cl)=[O:32])[CH2:30][CH2:29][CH2:28][CH2:27]1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(#N)C>[CH: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][CH2:27]1

Participants

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 at 0° C. Triethylamine (138 μl, 1.36 mmol) and cyclopentanecarbonyl chloride (138 μl, 1.36 mmol) were dropwise added to the solution, followed by stirring at room temperature for 2 hours. 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 purified by preparative TLC (ethyl acetate:n-hexane=1:3, v/v) to obtain the entitled compound (200 mg, 72%) as a colorless oil.

Workup

customthe solvent was evaporated away under reduced pressure
additionEthyl acetate was added to the resulting residue
washby washing with saturated brine
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
customthe solvent was evaporated away under reduced pressure
customThe resulting residue was purified by preparative TLC (ethyl acetate

Sources & evidence

ORD record: ord-cf4110348cc44c8b8529a264b1a4ef46
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Reaction notes

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