Chlorophenyl isocyanate → (S)-Methyl 2-(6-(5-(3-(2-chlorophenyl)ureido)pyridin-2-yl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

HRID 403985Notes

Reaction equation

HRID 403985 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:16]=[C:15]3[C:11]([CH2:12][N:13]([C@@H:18]([CH:23]([CH3:25])[CH3:24])[C:19]([O:21][CH3:22])=[O:20])[C:14]3=[O:17])=[CH:10][CH:9]=2)=[N:6][CH:7]=1.[Cl:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[N:33]=[C:34]=[O:35]>C1COCC1>[Cl:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[NH:33][C:34](=[O:35])[NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:16]=[C:15]3[C:11]([CH2:12][N:13]([C@@H:18]([CH:23]([CH3:25])[CH3:24])[C:19]([O:21][CH3:22])=[O:20])[C:14]3=[O:17])=[CH:10][CH:9]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 76833Chlorophenyl isocyanateHCID 131731548(S)-Methyl 2-(6-(5-aminopyridin-2-yl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

Product 1

HCID 131731549(S)-Methyl 2-(6-(5-(3-(2-chlorophenyl)ureido)pyridin-2-yl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound of example 392 (100 mg, 0.295 mmol) was dissolved in 3 mL THF and to this reaction mixture, 2-chlorophenyl isocyanate (49.83 mg, 0.324 mmol) was added and stirred at room temperature for 8-10 h. The reaction mixture was concentrated and purified by column chromatography (silica gel, 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 (silica gel, 30-40% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-38c1d325d44648bea7a6cd6bef05d10a
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Reaction notes

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