Water → HCID 70816640, compound

HRID 1843035Notes

Reaction equation

HRID 1843035 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([F:12])[CH:3]=1.[Cl:13][C:14]1[CH:15]=[C:16]([N:20]2[C:24]([CH2:25][NH:26][C:27](=O)[O:28]C3C=CC=CC=3)=[CH:23][C:22]([C:36]([F:39])([F:38])[F:37])=[N:21]2)[CH:17]=[CH:18][CH:19]=1.O>C(#N)C.CN(C1C=CN=CC=1)C>[Cl:13][C:14]1[CH:15]=[C:16]([N:20]2[C:24]([CH2:25][NH:26][C:27](=[O:28])[NH:1][C:2]3[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([F:12])[CH:3]=3)=[CH:23][C:22]([C:36]([F:37])([F:38])[F:39])=[N:21]2)[CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 962WaterHCID 21957875Methyl 4-amino-2-fluorobenzoateHCID 68941786HCID 68941786, compound

Product 1

HCID 70816640HCID 70816640, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of methyl 4-amino-2-fluorobenzoate (870 mg, 5.143 mmol) in acetonitrile was added DMAP (691 mg, 5.657 mmol) and phenyl (1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methylcarbamate (2036 mg, 5.143 mmol) at room temperature. The reaction mixture was refluxed overnight and then cooled to room temperature. The mixture was added water and extracted with EtOAC. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by column chromatography to give pure methyl 4-(3-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)ureido)-2-fluorobenzoate (1.3 g, 54%).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. extractionextracted with EtOAC
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-cfbba4e3cb044bfa989814f9bb692722
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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