Water → HCID 25233812, compound

HRID 1945178Notes

Reaction equation

HRID 1945178 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:10]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]([CH3:21])[CH3:20])[C:14]=1[NH:22][C:23]([NH:25][CH2:26][C:27]1([NH:32][C:33]2[CH:38]=[CH:37][C:36](I)=[CH:35][CH:34]=2)[CH2:31][CH2:30][CH2:29][CH2:28]1)=[O:24])([CH3:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+].O>C1(C)C=CC=CC=1>[C:36]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:35]=[CH:34][C:33]([NH:32][C:27]2([CH2:26][NH:25][C:23]([NH:22][C:14]3[C:13]([CH:10]([CH3:12])[CH3:11])=[CH:18][CH:17]=[CH:16][C:15]=3[CH:19]([CH3:21])[CH3:20])=[O:24])[CH2:28][CH2:29][CH2:30][CH2:31]2)=[CH:38][CH:37]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 25233810HCID 25233810, compound

Product 1

HCID 25233812HCID 25233812, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

45 mg (0.37 mmol) of phenylboronic acid are added to 150 mg (0.29 mmol) of 1-(2,6-diisopropylphenyl)-3-[1-(4-iodophenylamino)-cyclopentylmethyl]-urea (Example 6d) in 20 ml of toluene. 370 μl (0.74 mmol) of a 2M aqueous solution of potassium carbonate are added. The reaction medium is degassed with nitrogen for 20 min, then 10 mg (8.65 μmol) of tetrakis-(triphenylphosphine)palladium are added. The medium is heated at 100° C. for 6 hours, then at ambient temperature for 10 days. It is then poured into water and extracted with ethyl acetate. The organic phases are combined and washed with water. They are dried over sodium sulfate. The solvents are evaporated and the residue is chromatographed on silica gel (heptane/ethyl acetate, 80/20 v/v). 78 mg of 1-[1-(biphenyl-4-ylamino)cyclopentylmethyl]-3-(2,6-diisopropyl-phenyl)-urea are obtained in the form of a white solid. (M.Pt.=198° C., Yield=57%).

Workup

  1. customThe reaction medium is degassed with nitrogen for 20 min
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. dry with materialThey are dried over sodium sulfate
  5. customThe solvents are evaporated
  6. customthe residue is chromatographed on silica gel (heptane/ethyl acetate, 80/20 v/v)

Sources & evidence

ORD record
ord-534e83ccb1f24ee593acd0027f4485b8
Source dataset
uspto-grants-2013_03
Patent number
US08394990B2

Reaction notes

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