Ethanol → {4-[2-(4-Fluoro-phenyl)-cyclohex-1-enyl]-pyridin-2-yl}-urea

HRID 1023472Notes

Reaction equation

HRID 1023472 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[C:14]2[CH:19]=[CH:18][N:17]=[C:16]([NH2:20])[CH:15]=2)=[CH:4][CH:3]=1.[C:21]([N:29]=C=O)(=[O:28])C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].C(O)C>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[C:14]2[CH:19]=[CH:18][N:17]=[C:16]([NH:20][C:21]([NH2:29])=[O:28])[CH:15]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 78210Benzoyl isocyanateHCID 690855804-[2-(4-Fluoro-phenyl)-cyclohex-1-enyl]-pyridin-2-ylamine

Product 1

HCID 69085978{4-[2-(4-Fluoro-phenyl)-cyclohex-1-enyl]-pyridin-2-yl}-ureaYield 86.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

A sealed 8 mL vial is charged with a solution of 4-[2-(4-Fluoro-phenyl)-cyclohex-1-enyl]-pyridin-2-ylamine (11 mg, 0.041 mmol) in methylene chloride (2 mL). Then benzoyl isocynate (9.0 mg, 0.06 mmol) is added. The resulting mixture is allowed to stir at 50° C. for 1 hour. The solvent is then carefully removed before potassium carbonate (6.8 mg, 0.049 mmol) and ethanol (1 mL) are added. The resulting reaction is allowed to stir at 85° C. for 30 min. Solvent is removed and the crude is purified by silica flash column chromatography using MeOH in DCM (gradient from 0% to 5%) to give 11 mg of the titled product.

Workup

  1. additionare added
  2. customThe resulting reaction
  3. stirringto stir at 85° C. for 30 min
  4. customSolvent is removed
  5. customthe crude is purified by silica flash column chromatography

Sources & evidence

ORD record
ord-9a6c72c87fa24503a21bde3df77a3e45
Source dataset
uspto-grants-2014_05
Patent number
US08722709B2

Reaction notes

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