Cyclohexyl isocyanate → 1,3-Dicyclohexyl-1-(2-phenyl-2H-indazol-3-yl)-urea

HRID 1690508Notes

Reaction equation

HRID 1690508 reaction equation
[CH:1]1([N:7]=[C:8]=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:10]1([NH:16][C:17]2[N:18]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:19]=[C:20]3[C:25]=2[CH:24]=[CH:23][CH:22]=[CH:21]3)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>C1(C)C=CC=CC=1>[CH:10]1([N:16]([C:17]2[N:18]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:19]=[C:20]3[C:25]=2[CH:24]=[CH:23][CH:22]=[CH:21]3)[C:8]([NH:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:9])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 18502Cyclohexyl isocyanate2×HCID 12318206N-Cyclohexyl-2-phenyl-2H-indazol-3-amine

Product 1

HCID 451106131,3-Dicyclohexyl-1-(2-phenyl-2H-indazol-3-yl)-ureaYield 27%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Cyclohexylisocyanate (13 ul, 0.1 mmol; [3173-53-3]) was added at ambient temperature to a solution of cyclohexyl-(2-phenyl-2H-indazol-3-yl)-amine (30 mg, 0.1 mmol) in toluene (0.4 ml) under an argon atmosphere. The solution was heated under reflux conditions for 12 h, cyclohexylisocyanate (7 μl, 60 μmol; [3173-53-3]) was added and heating was continued for further 6 h. The solvent was removed under reduced pressure to give a brown oil which was purified by preparative thin layer chromatography (silica gel, iPrOAc/heptane) to give the title compound (11 mg, 26 μmol; 27%) as off-white solid. MS: m/e=417.4 [M+H+].

Workup

  1. temperatureThe solution was heated under reflux conditions for 12 h
  2. temperatureheating
  3. customThe solvent was removed under reduced pressure
  4. customto give a brown oil which
  5. customwas purified by preparative thin layer chromatography (silica gel, iPrOAc/heptane)

Sources & evidence

ORD record
ord-9eb45dd866fa404db08a274ca0490603
Source dataset
uspto-grants-2012_04
Patent number
US08153663B2

Reaction notes

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