Isobutyric Acid → HCID 66690851, compound

HRID 592308Notes

Reaction equation

HRID 592308 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:16]([O:18][CH3:19])=[O:17])[CH:5]=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[C:7]=1[OH:8].[C:20](O)(=O)[CH:21]([CH3:23])[CH3:22].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.ClC(Cl)(Cl)C#N>C(#N)C>[F:15][C:12]1[CH:11]=[CH:10][C:9]([C:6]2[C:7]3[O:8][C:20]([CH:21]([CH3:23])[CH3:22])=[N:1][C:2]=3[CH:3]=[C:4]([C:16]([O:18][CH3:19])=[O:17])[CH:5]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 6590Isobutyric AcidHCID 11011TrichloroacetonitrileHCID 11776TriphenylphosphineHCID 66690544HCID 66690544, compound

Product 1

HCID 66690851HCID 66690851, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of methyl 5-amino-4′-fluoro-6-hydroxybiphenyl-3-carboxylate (10.0 mg, 38.0 μmol), and isobutyric acid (2.60 mg, 29.0 μmol), and solid support triphenylphosphine (75% by weight; 40.2 mg, 0.12 mmol) in acetonitrile (0.38 mL) was added trichloroacetonitrile (7.68 μL, 77.0 μmol). The mixture was heated in a microwave reactor for 15 min at 150° C. The mixture was cooled to ambient temperature, filtered and concentrated. Purification by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (5 mg). LC-MS [M+1]=332.1.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customPurification by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-c6338a1c28094b24b89b4e4dc7cb888f
Source dataset
uspto-grants-2016_01
Patent number
US09238647B2

Reaction notes

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