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

HRID 404003Notes

Reaction equation

HRID 404003 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.[CH2:35]1[C:43]2[C:38](=[CH:39][C:40]([NH:44][C:45](=[O:75])[NH:46][C:47]3[CH:52]=[CH:51][C:50]([C:53]4[CH:61]=[C:60]5[C:56]([CH2:57][N:58]([C@@H:63]([CH:68]([CH3:70])[CH3:69])[C:64]([O:66]C)=[O:65])[C:59]5=[O:62])=[CH:55][CH:54]=4)=[C:49]([C:71]([F:74])([F:73])[F:72])[CH:48]=3)=[CH:41][CH:42]=2)[CH2:37][CH2:36]1>>[CH2:35]1[C:43]2[C:38](=[CH:39][C:40]([NH:44][C:45](=[O:75])[NH:46][C:47]3[CH:52]=[CH:51][C:50]([C:53]4[CH:61]=[C:60]5[C:56]([CH2:57][N:58]([C@@H:63]([CH:68]([CH3:70])[CH3:69])[C:64]([OH:66])=[O:65])[C:59]5=[O:62])=[CH:55][CH:54]=4)=[C:49]([C:71]([F:72])([F:73])[F:74])[CH:48]=3)=[CH:41][CH:42]=2)[CH2:37][CH2:36]1

Participants

3

Reactant 2

HCID 70975553(S)-2-(6-(5-(3-(2-Chlorophenyl)ureido)pyridin-2-yl)-1-oxoisoindolin-2-yl)-3-methylbutanoic acidHCID 131731558(S)-Methyl 2-(6-(4-(3-(2,3-dihydro-1H-inden-5-yl)ureido)-2-(trifluoromethyl)phenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

Product 1

HCID 67306787(S)-2-(6-(4-(3-(2,3-Dihydro-1H-inden-5-yl)ureido)-2-(trifluoromethyl)phenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoic acidYield 97%

Procedure

The compound of example 420 was prepared analogous to the compound of example 394 by hydrolysis of the compound of example 419.

Sources & evidence

ORD record
ord-8c5a1a59c23e48438b1229c182158264
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Reaction notes

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