Ethyl 5-phenyl-1,3-oxazole-2-carboxylate → (S)-Methyl 3-methyl-2-(1-oxo-6-(5-(5-phenyloxazole-2-carboxamido)pyridin-2-yl)isoindolin-2-yl)butanoate

HRID 404106Notes

Reaction equation

HRID 404106 reaction equation
CC(C)[C@H](N1CC2C(=CC(C3C=CC(NC(C4SC(C5C=CC=CC=5)=CN=4)=O)=CC=3)=CC=2)C1=O)C(OC)=O.[NH2:39][C:40]1[CH:41]=[CH:42][C:43]([C:46]2[CH:54]=[C:53]3[C:49]([CH2:50][N:51]([C@@H:56]([CH:61]([CH3:63])[CH3:62])[C:57]([O:59][CH3:60])=[O:58])[C:52]3=[O:55])=[CH:48][CH:47]=2)=[N:44][CH:45]=1.[C:64]1([C:70]2[O:74][C:73]([C:75](OCC)=[O:76])=[N:72][CH:71]=2)[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1>>[CH3:62][CH:61]([CH3:63])[C@H:56]([N:51]1[CH2:50][C:49]2[C:53](=[CH:54][C:46]([C:43]3[CH:42]=[CH:41][C:40]([NH:39][C:75]([C:73]4[O:74][C:70]([C:64]5[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=5)=[CH:71][N:72]=4)=[O:76])=[CH:45][N:44]=3)=[CH:47][CH:48]=2)[C:52]1=[O:55])[C:57]([O:59][CH3:60])=[O:58]

Participants

4

Reactant 3

HCID 13388477Ethyl 5-phenyl-1,3-oxazole-2-carboxylateHCID 123332092(S)-Methyl 3-methyl-2-(1-oxo-6-(4-(5-phenylthiazole-2-carboxamido)phenyl)isoindolin-2-yl)butanoateHCID 131731548(S)-Methyl 2-(6-(5-aminopyridin-2-yl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

Product 1

HCID 123156697(S)-Methyl 3-methyl-2-(1-oxo-6-(5-(5-phenyloxazole-2-carboxamido)pyridin-2-yl)isoindolin-2-yl)butanoateYield 83%

Procedure

The compound of example 634 was prepared analogous to the compound of example 611 by reaction of compound of example 392 with ethyl 5-phenyloxazole-2-carboxylate.

Sources & evidence

ORD record
ord-36470e9e9a5a4831884721b4eddf7652
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Reaction notes

Loading…