3-(Trifluoromethyl)phenyl isocyanate → (2-{4-[3-(3-Trifluoromethyl-phenyl)-ureido]-imidazol-1-yl}ethyl)-carbamic acid tert-butyl ester

HRID 1818934Notes

Reaction equation

HRID 1818934 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][CH2:9][N:10]1[CH:14]=[C:13]([NH2:15])[N:12]=[CH:11]1)([CH3:4])([CH3:3])[CH3:2].[F:17][C:18]([F:29])([F:28])[C:19]1[CH:20]=[C:21]([N:25]=[C:26]=[O:27])[CH:22]=[CH:23][CH:24]=1>ClCCl>[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][CH2:9][N:10]1[CH:14]=[C:13]([NH:15][C:26]([NH:25][C:21]2[CH:22]=[CH:23][CH:24]=[C:19]([C:18]([F:17])([F:28])[F:29])[CH:20]=2)=[O:27])[N:12]=[CH:11]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 68425567Tert-butyl 2-(4-amino-1H-imidazol-1-YL)ethylcarbamate

Product 1

HCID 68422862(2-{4-[3-(3-Trifluoromethyl-phenyl)-ureido]-imidazol-1-yl}ethyl)-carbamic acid tert-butyl esterYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 39.3 in dichloromethane under nitrogen was added 3-trifluoromethylphenyl isocyanate dropwise. After about 0.1 hour, a white precipitate formed. The precipitate was filtered off, washed with dichloromethane and dried under high-vacuum to yield 485 mg (75%) of (2-{4-[3-(3-trifluoromethyl-phenyl)-ureido]-imidazol-1-yl}ethyl)-carbamic acid tert-butyl ester (compound 39.4) as a white solid, ES (+) MS m/e=414 (M+H+).

Workup

  1. customa white precipitate formed
  2. filtrationThe precipitate was filtered off
  3. washwashed with dichloromethane
  4. customdried under high-vacuum

Sources & evidence

ORD record
ord-328b9da48c0f4f2790743585c9a0f2fc
Source dataset
uspto-grants-2009_10
Patent number
US07601725B2

Reaction notes

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