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

HRID 2277415Notes

Reaction equation

HRID 2277415 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:12])[CH:8]=[C:9]([NH2:11])[N:10]=1)=[O:5])[CH3:2].[F:13][C:14]([F:26])([F:25])[O:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]=[C:23]=[O:24])=[CH:18][CH:17]=1>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:12])[CH:8]=[C:9]([NH:11][C:23]([NH:22][C:19]2[CH:20]=[CH:21][C:16]([O:15][C:14]([F:13])([F:25])[F:26])=[CH:17][CH:18]=2)=[O:24])[N:10]=1)=[O:5])[CH3:2]

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

1.22 g (3.61 mmol) of 4-amino-1-methyl-1H-imidazole-2-carboxylic acid ethyl ester (synthesis analogous to Example 1A, Stage 3, or else according to Tetrahedron Lett. 2003, 44, 1607 and literature cited there) is mixed in 50 ml of THF under argon with 1.46 g (7.21 mmol) of 4-(trifluoromethoxy)phenylisocyanate and stirred overnight at room temperature. The reaction mixture is filtered, the filtrate is concentrated by evaporation in a vacuum, and it is purified chromatographically.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated by evaporation in a vacuum, and it
  3. customis purified chromatographically

Sources & evidence

ORD record
ord-d89ace771daa4b23ae15d87c3b5ce8b0
Source dataset
uspto-grants-2015_09
Patent number
US09133165B2

Reaction notes

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