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

HRID 403886Notes

Reaction equation

HRID 403886 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[S:35])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[C:22](=[O:26])[N:21]([C@@H:27]([CH:32]([CH3:34])[CH3:33])[C:28]([O:30][CH3:31])=[O:29])[CH2:20]3)=[CH:13][CH:12]=1.NC1C=CC(C2C=C3C(=CC=2)[C:48](=[O:52])N([C@@H](C(C)C)C(OC)=O)C3)=CC=1.COC1C=CC(N=C=S)=CC=1>>[CH3:48][O:52][C:6]1[CH:5]=[CH:4][C:3]([NH:8][C:9](=[S:35])[NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[C:22](=[O:26])[N:21]([C@@H:27]([CH:32]([CH3:34])[CH3:33])[C:28]([O:30][CH3:31])=[O:29])[CH2:20]4)=[CH:13][CH:12]=2)=[CH:2][CH:7]=1

Participants

4

Reactant 3

HCID 752934-Methoxyphenyl isothiocyanateHCID 131731499(S)-Methyl 2-(5-(4-aminophenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoateHCID 131731509(S)-Methyl 2-(5-(4-(3-(2-fluorophenyl)thioureido)phenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

Product 1

HCID 131731511(S)-Methyl 2-(5-(4-(3-(4-methoxyphenyl)thioureido)phenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

Procedure

The compound of example 260 was prepared analogous to compound of example 256 by reaction of compound of example 223 with 4-methoxy phenyl isothiocyanate. The compound of example 260 was used directly without isolation for the preparation of compound of example 261.

Sources & evidence

ORD record
ord-84bc97a3acda471286150ea2b32bbabb
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Reaction notes

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