3-Cyanophenyl isothiocyanate → (S)-Methyl 2-(6-(4-(3-(3-cyanophenyl)thioureido)phenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

HRID 403749

Reaction equation

HRID 403749 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.[NH2:36][C:37]1C=CC(C2C=C3C(CN([C@@H](C(C)C)C(OC)=O)C3=O)=CC=2)=CC=1.C(C1C=C(N=C=S)C=CC=1)#N>>[C:37]([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:25]=[C:24]4[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]4=[O:26])=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)[CH:4]=[CH:5][CH:6]=1)#[N:36]

Participants

4

Reactant 3

HCID 765783-Cyanophenyl 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 131731456(S)-Methyl 2-(6-(4-(3-(3-cyanophenyl)thioureido)phenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

Procedure

The compound of example 69 was prepared analogous to compound of example 51 by reaction of compound of example 6 with 3-cyanophenyl isothiocyanate. The compound of example 69 was used directly without isolation for the preparation of compound of example 70.

Sources & evidence

ORD record
ord-d57459f736b643af94c3767fd30b876d
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Linked notes

Loading…