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

HRID 403882

Reaction equation

HRID 403882 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][CH:30]=[CH:29][C:28]=1[N:33]=[C:34]=[S:35]>C1COCC1>[F:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[NH:33][C:34](=[S:35])[NH: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

Participants

4

Reactant 2

HCID 975202-Fluorophenyl isothiocyanateHCID 131731499(S)-Methyl 2-(5-(4-aminophenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

Product 1

HCID 131731509(S)-Methyl 2-(5-(4-(3-(2-fluorophenyl)thioureido)phenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound of example 223 (0.150 g, 0.000443 mol) was taken in THF (3 mL) and 2-fluorophenyl isothiocyanate (0.074 g, 0.000448 mol) was added and stirred at room temperature for 8-10 h. The reaction mixture was concentrated and directly used for preparation of compound of example 257.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customdirectly used for preparation of compound of example 257

Sources & evidence

ORD record
ord-74667683940b4f4cb7e61ebb6a6d3d0c
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Linked notes

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