3-Fluoro-4-methylphenyl isocyanate → Ethyl 4-({[(3-fluoro-4-methylphenyl)amino]carbonyl}amino)-1-methyl-1H-imidazole-2-carboxylate

HRID 499906Notes

Reaction equation

HRID 499906 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:5]([CH3:7])[CH:6]=1.[F:13][C:14]1[CH:15]=[C:16]([N:21]=[C:22]=[O:23])[CH:17]=[CH:18][C:19]=1[CH3:20]>C1COCC1>[F:13][C:14]1[CH:15]=[C:16]([NH:21][C:22]([NH:1][C:2]2[N:3]=[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:5]([CH3:7])[CH:6]=2)=[O:23])[CH:17]=[CH:18][C:19]=1[CH3:20]

Participants

4

Reactant 2

HCID 27373983-Fluoro-4-methylphenyl isocyanateHCID 7006687ethyl 4-amino-1-methyl-1H-imidazole-2-carboxylate

Product 1

HCID 11709531Ethyl 4-({[(3-fluoro-4-methylphenyl)amino]carbonyl}amino)-1-methyl-1H-imidazole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.30 g (3.84 mmol) of ethyl 4-amino-1-methyl-1H-imidazole-2-carboxylate (synthesis analogous to Example 4A, stage 3, or else according to Tetrahedron Lett. 2003, 44, 1607 and literature cited therein) are mixed in 50 ml of THF with 1.16 g (7.68 mmol) of 3-fluoro-4-methylphenyl isocyanate under argon and stirred at room temperature overnight. The reaction mixture is filtered, and the filtrate is concentrated in vacuo and purified by preparative HPLC. The residue from filtration affords together with the product obtained after the HPLC purification 715 mg of product.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated in vacuo
  3. custompurified by preparative HPLC
  4. filtrationThe residue from filtration
  5. customaffords together with the product
  6. customobtained
  7. customafter the HPLC purification 715 mg of product

Sources & evidence

ORD record
ord-a72d78cd7c874688ad6702f8a7abc02e
Source dataset
uspto-grants-2010_08
Patent number
US07767704B2

Reaction notes

Loading…