Diethyl Ether → HCID 53240508, compound

HRID 1023622Notes

Reaction equation

HRID 1023622 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[OH:11])[C:6]#[N:7])[CH3:2].F[C:13]1[N:18]=[CH:17][C:16]([N:19]2[C:23](=[O:24])[C:22]([CH3:26])([CH3:25])[NH:21][C:20]2=[O:27])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)C>CN(C)C=O.O>[CH3:25][C:22]1([CH3:26])[C:23](=[O:24])[N:19]([C:16]2[CH:15]=[CH:14][C:13]([O:11][C:10]3[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=3[CH2:1][CH3:2])=[N:18][CH:17]=2)[C:20](=[O:27])[NH:21]1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 67235281HCID 67235281, compound2×HCID 683225173-Ethyl-4-hydroxybenzonitrile2×

Product 1

HCID 53240508HCID 53240508, compoundYield 33.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

3-ethyl-4-hydroxybenzonitrile (Intermediate 115, 70 mg) was dissolved in 2 mL of dimethylformamide. 3-(6-fluoro-3-pyridinyl)-5,5-dimethyl-2,4-imidazolidinedione (Intermediate 106, 102 mg) and potassium carbonate (126 mg, 0.915 mmol) were added. The reaction mixture was stirred at 120° C. during 96 hours. Some diethyl ether (4 mL) and water (4 mL) were added. The aqueous layer was extracted 4 times with diethyl ether. The gathered organic layers were dried over sodium sulphate and evaporated giving a residue which was purified by flash chromatography on silica gel (companion system, 12 g Si cartridge) using as eluent a gradient cyclohexane/ethyl acetate 100/0, then from 100/0 to 55/45. Evaporation afforded the title compound (54 mg) as a white solid.

Workup

  1. extractionThe aqueous layer was extracted 4 times with diethyl ether
  2. dry with materialThe gathered organic layers were dried over sodium sulphate
  3. customevaporated
  4. customgiving a residue which
  5. customwas purified by flash chromatography on silica gel (companion system, 12 g Si cartridge)
  6. customEvaporation

Sources & evidence

ORD record
ord-2921ffb6e28c40cb9cbb407af36585ed
Source dataset
uspto-grants-2014_05
Patent number
US08722695B2

Reaction notes

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