4-Fluorophenyl isocyanate → (S)-Methyl 2-(5-(4-(3-(4-fluorophenyl)ureido)phenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

HRID 403862Notes

Reaction equation

HRID 403862 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[C:13](=[O:17])[N:12]([C@@H:18]([CH:23]([CH3:25])[CH3:24])[C:19]([O:21][CH3:22])=[O:20])[CH2:11]3)=[CH:4][CH:3]=1.[F:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]=[C:34]=[O:35])=[CH:29][CH:28]=1>ClCCl>[F:26][C:27]1[CH:32]=[CH:31][C:30]([NH:33][C:34](=[O:35])[NH:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:9]=[C:10]4[C:14](=[CH:15][CH:16]=3)[C:13](=[O:17])[N:12]([C@@H:18]([CH:23]([CH3:25])[CH3:24])[C:19]([O:21][CH3:22])=[O:20])[CH2:11]4)=[CH:4][CH:3]=2)=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 709554-Fluorophenyl isocyanateHCID 131731499(S)-Methyl 2-(5-(4-aminophenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

Product 1

HCID 123620640(S)-Methyl 2-(5-(4-(3-(4-fluorophenyl)ureido)phenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound of example 223 (0.230 g, 0.00153 mol) was dissolved in 5 mL dichloromethane and to this reaction mixture, 4-fluorophenyl isocyanate (0.102 g, 0.000744 mol) was added and stirred at room temperature for 8-10 h. The reaction mixture was concentrated and purified by column chromatography (silicagel, 30-40% ethyl acetate in petroleum ether to obtain the title compound.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by column chromatography (silicagel, 30-40% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-c52c1e7707514cd7a142d1dcc16fb45e
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Reaction notes

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