4-(Trifluoromethyl)phenyl isocyanate → (S)-Methyl 3-methyl-2-(1-oxo-5-(4-(3-(4-(trifluoromethyl)phenyl)ureido)phenyl)isoindolin-2-yl)butanoate

HRID 403870Notes

Reaction equation

HRID 403870 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O: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:3]=1.NC1C=CC(C2C=C3C(=CC=2)C(=O)N([C@@H](C(C)C)C(OC)=O)C3)=CC=1.[F:61][C:62]([F:73])([F:72])C1C=CC(N=C=O)=CC=1>>[CH3:33][CH:32]([CH3:34])[C@H:27]([N:21]1[CH2:20][C:19]2[C:23](=[CH:24][CH:25]=[C:17]([C:14]3[CH:13]=[CH:12][C:11]([NH:10][C:9]([NH:8][C:5]4[CH:6]=[CH:7][C:2]([C:62]([F:73])([F:72])[F:61])=[CH:3][CH:4]=4)=[O:35])=[CH:16][CH:15]=3)[CH:18]=2)[C:22]1=[O:26])[C:28]([O:30][CH3:31])=[O:29]

Participants

4

Reactant 3

HCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 123620640(S)-Methyl 2-(5-(4-(3-(4-fluorophenyl)ureido)phenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoateHCID 131731499(S)-Methyl 2-(5-(4-aminophenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

Product 1

HCID 131731504(S)-Methyl 3-methyl-2-(1-oxo-5-(4-(3-(4-(trifluoromethyl)phenyl)ureido)phenyl)isoindolin-2-yl)butanoate

Procedure

The compound of example 244 was prepared analogous to compound of example 224 by reaction of compound of example 223 with 4-trifluoromethyl phenyl isocyanate. The compound of example 244 was used directly without isolation for the preparation of compound of example 245.

Sources & evidence

ORD record
ord-476226d98aa4407397f1f7ad5299d9d3
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Reaction notes

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