p-Tolyl isothiocyanate → (S)-Methyl 3-methyl-2-(1-oxo-6-(4-(3-p-tolylthioureido)phenyl)isoindolin-2-yl)butanoate

HRID 403736

Reaction equation

HRID 403736 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:25]=[C:24]3[C:20]([CH2:21][N:22]([C@@H:27]([CH:32]([CH3:34])[CH3:33])[C:28]([O:30][CH3:31])=[O:29])[C:23]3=[O:26])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1.N[C:37]1C=CC(C2C=C3C(CN([C@@H](C(C)C)C(OC)=O)C3=O)=CC=2)=CC=1.CC1C=CC(N=C=S)=CC=1>>[CH3:33][CH:32]([CH3:34])[C@H:27]([N:22]1[CH2:21][C:20]2[C:24](=[CH:25][C:17]([C:14]3[CH:15]=[CH:16][C:11]([NH:10][C:9]([NH:8][C:3]4[CH:4]=[CH:5][C:6]([CH3:37])=[CH:7][CH:2]=4)=[S:35])=[CH:12][CH:13]=3)=[CH:18][CH:19]=2)[C:23]1=[O:26])[C:28]([O:30][CH3:31])=[O:29]

Participants

4

Reactant 3

HCID 12149p-Tolyl isothiocyanateHCID 53303391(S)-Methyl 2-(6-(4-(3-(2-fluorophenyl)thioureido)phenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoateHCID 131731441(S)-Methyl 2-(6-(4-aminophenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

Product 1

HCID 53303392(S)-Methyl 3-methyl-2-(1-oxo-6-(4-(3-p-tolylthioureido)phenyl)isoindolin-2-yl)butanoate

Procedure

The compound of example 53 was prepared analogous to compound of example 51 by reaction of compound of example 6 with 4-methyl phenyl isothiocyanate. The compound of example 53 was used directly without isolation for the preparation of compound of example 54.

Sources & evidence

ORD record
ord-2472f080008b425b8d41078857ffd60c
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Linked notes

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