Phenyl isocyanate → 1-(7,7-Dimethyl-6-oxo-5-pentyl-1,5,6,7-tetrahydro-imidazo[4,5-f]indol-2-yl)-3-phenyl-urea

HRID 2235470Notes

Reaction equation

HRID 2235470 reaction equation
[NH2:1][C:2]1[NH:21][C:5]2=[CH:6][C:7]3[C:8]([CH3:20])([CH3:19])[C:9](=[O:18])[N:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:11]=3[CH:12]=[C:4]2[N:3]=1.[C:22]1([N:28]=[C:29]=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CC(C)=O>[CH3:19][C:8]1([CH3:20])[C:7]2[CH:6]=[C:5]3[NH:21][C:2]([NH:1][C:29]([NH:28][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[O:30])=[N:3][C:4]3=[CH:12][C:11]=2[N:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:9]1=[O:18]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 593008242-Amino-7,7-dimethyl-5-pentyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one

Product 1

HCID 593008291-(7,7-Dimethyl-6-oxo-5-pentyl-1,5,6,7-tetrahydro-imidazo[4,5-f]indol-2-yl)-3-phenyl-ureaYield 63.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of D5 (172 mg) and phenyl isocyanate (72 mg; 0.6 mmol) in acetone (3 ml) is stirred at RT for 3 days. Acetone is evaporated and the residue is purified by flash chromatography on silica gel eluted with CH2Cl2/MeOH (20:1) to give the desired compound (154 mg).

Workup

  1. customAcetone is evaporated
  2. customthe residue is purified by flash chromatography on silica gel
  3. washeluted with CH2Cl2/MeOH (20:1)

Sources & evidence

ORD record
ord-c55a761541d94927947765f25eff7561
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

Loading…