p-(Trifluoromethoxy)phenyl isocyanate → Ethyl 1-methyl-4-[({[4-(trifluoromethoxy)phenyl]amino}carbonyl)amino]-1H-imidazole-2-carboxylate

HRID 2074073Notes

Reaction equation

HRID 2074073 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]=[C:11]=[O:12])=[CH:6][CH:5]=1.[NH2:15][C:16]1[N:17]=[C:18]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:19]([CH3:21])[CH:20]=1>C1COCC1>[CH3:21][N:19]1[CH:20]=[C:16]([NH:15][C:11]([NH:10][C:7]2[CH:6]=[CH:5][C:4]([O:3][C:2]([F:13])([F:14])[F:1])=[CH:9][CH:8]=2)=[O:12])[N:17]=[C:18]1[C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

4

Reactant 2

HCID 92298p-(Trifluoromethoxy)phenyl isocyanateHCID 7006687ethyl 4-amino-1-methyl-1H-imidazole-2-carboxylate

Product 1

HCID 59421902Ethyl 1-methyl-4-[({[4-(trifluoromethoxy)phenyl]amino}carbonyl)amino]-1H-imidazole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under argon, 1.46 g (7.21 mmol) of 4-(trifluoromethoxy)phenyl isocyanate are added to 1.22 g (3.61 mmol) of ethyl 4-amino-1-methyl-1H-imidazole-2-carboxylate (synthesis in analogy to Example 4A step 3, or also according to Tetrahedron Lett. 2003, 44, 1607 and the literature cited therein) in 50 ml of THF, and the mixture is stirred at room temperature overnight. The reaction mixture is filtered and the filtrate is concentrated in vacuo and purified chromatographically.

Workup

  1. customsynthesis in analogy to Example 4A step 3
  2. filtrationThe reaction mixture is filtered
  3. concentrationthe filtrate is concentrated in vacuo
  4. custompurified chromatographically

Sources & evidence

ORD record
ord-721dd9feeb6843cf82e5f636be6397c1
Source dataset
uspto-grants-2011_04
Patent number
US07919489B2

Reaction notes

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