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Methyl 4-(1,3-oxazol-5-yl)benzoate → (S)-Methyl 3-methyl-2-(6-(4-(4-(oxazol-5-yl)benzamido)phenyl)-1-oxoisoindolin-2-yl)butanoate

HRID 404097
Notes
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Reaction equation

HRID 404097 reaction equation
[CH3:1][CH:2]([CH3:38])[C@H:3]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][C:12]([C:17]3[CH:22]=[CH:21][C:20]([NH:23][C:24](C4SC(C5C=CC=CC=5)=CN=4)=[O:25])=[CH:19][CH:18]=3)=[CH:13][CH:14]=2)[C:9]1=[O:37])[C:4]([O:6][CH3:7])=[O:5].NC1C=CC(C2C=C3C(CN([C@@H](C(C)C)C(OC)=O)C3=O)=CC=2)=CC=1.[O:64]1[C:68]([C:69]2[CH:78]=[CH:77][C:72](C(OC)=O)=[CH:71][CH:70]=2)=[CH:67][N:66]=[CH:65]1>>[CH3:38][CH:2]([CH3:1])[C@H:3]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][C:12]([C:17]3[CH:18]=[CH:19][C:20]([NH:23][C:24](=[O:25])[C:72]4[CH:71]=[CH:70][C:69]([C:68]5[O:64][CH:65]=[N:66][CH:67]=5)=[CH:78][CH:77]=4)=[CH:21][CH:22]=3)=[CH:13][CH:14]=2)[C:9]1=[O:37])[C:4]([O:6][CH3:7])=[O:5]
ParticipantsProcedureSources & evidenceReaction notes

Participants

4

Reactant 3

HCID 1477779Methyl 4-(1,3-oxazol-5-yl)benzoateHCID 123332092(S)-Methyl 3-methyl-2-(1-oxo-6-(4-(5-phenylthiazole-2-carboxamido)phenyl)isoindolin-2-yl)butanoateHCID 131731441(S)-Methyl 2-(6-(4-aminophenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

Product 1

HCID 131731590(S)-Methyl 3-methyl-2-(6-(4-(4-(oxazol-5-yl)benzamido)phenyl)-1-oxoisoindolin-2-yl)butanoateYield 58%

Procedure

The compound of example 621 was prepared analogous to the compound of example 611 by reaction of compound of example 6 with commercially available methyl 4-(oxazol-5-yl)benzoate (Ryan Scientific, USA).

Sources & evidence

ORD record
ord-316bae5aa61047c18157922ec84ec979
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08748426B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes