(S)-2-(6-(5-(3-(2-Chlorophenyl)ureido)pyridin-2-yl)-1-oxoisoindolin-2-yl)-3-methylbutanoic acid → (S)-2-(6-(4-(3-(3,4-Difluorophenyl)ureido)-2-(trifluoromethyl)phenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoic acid

HRID 404002Notes

Reaction equation

HRID 404002 reaction equation
ClC1C=CC=CC=1NC(=O)NC1C=CC(C2C=C3C(CN([C@@H](C(C)C)C(O)=O)C3=O)=CC=2)=NC=1.[F:35][C:36]1[CH:37]=[C:38]([NH:43][C:44](=[O:74])[NH:45][C:46]2[CH:51]=[CH:50][C:49]([C:52]3[CH:60]=[C:59]4[C:55]([CH2:56][N:57]([C@@H:62]([CH:67]([CH3:69])[CH3:68])[C:63]([O:65]C)=[O:64])[C:58]4=[O:61])=[CH:54][CH:53]=3)=[C:48]([C:70]([F:73])([F:72])[F:71])[CH:47]=2)[CH:39]=[CH:40][C:41]=1[F:42]>>[F:35][C:36]1[CH:37]=[C:38]([NH:43][C:44](=[O:74])[NH:45][C:46]2[CH:51]=[CH:50][C:49]([C:52]3[CH:60]=[C:59]4[C:55]([CH2:56][N:57]([C@@H:62]([CH:67]([CH3:69])[CH3:68])[C:63]([OH:65])=[O:64])[C:58]4=[O:61])=[CH:54][CH:53]=3)=[C:48]([C:70]([F:73])([F:71])[F:72])[CH:47]=2)[CH:39]=[CH:40][C:41]=1[F:42]

Participants

3

Reactant 2

HCID 70975553(S)-2-(6-(5-(3-(2-Chlorophenyl)ureido)pyridin-2-yl)-1-oxoisoindolin-2-yl)-3-methylbutanoic acidHCID 131731557(S)-Methyl 2-(6-(4-(3-(3,4-difluorophenyl)ureido)-2-(trifluoromethyl)phenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

Product 1

HCID 53302550(S)-2-(6-(4-(3-(3,4-Difluorophenyl)ureido)-2-(trifluoromethyl)phenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoic acidYield 87%

Procedure

The compound of example 418 was prepared analogous to the compound of example 394 by hydrolysis of the compound of example 417.

Sources & evidence

ORD record
ord-3472b9fcbe044c0fbc6400d75d76eb5d
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Reaction notes

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