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

HRID 403892

Reaction equation

HRID 403892 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(=O)N([C@@H](C(C)C)C(OC)=O)C3)=CC=1.[Cl:61]C1C=C(N=C=S)C=CC=1>>[Cl:61][C:7]1[CH:2]=[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:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 754493-Chlorophenyl 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 131731513(S)-Methyl 2-(5-(4-(3-(3-chlorophenyl)thioureido)phenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

Procedure

The compound of example 266 was prepared analogous to compound of example 256 by reaction of compound of example 223 with 3-chlorophenyl isothiocyanate. The compound of example 266 was used directly without isolation for the preparation of compound of example 267.

Sources & evidence

ORD record
ord-b3346d5b7e0944819d8f06e5da2c85b4
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Linked notes

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