Ethyl 3-(4-chlorophenyl)isoxazole-5-carboxylate → (S)-Methyl 2-(6-(4-(3-(4-chlorophenyl)isoxazole-5-carboxamido)phenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

HRID 404093Notes

Reaction equation

HRID 404093 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]([C:26]4SC(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.[Cl:64][C:65]1[CH:70]=[CH:69][C:68]([C:71]2[CH:75]=C(C(OCC)=O)[O:73][N:72]=2)=[CH:67][CH:66]=1>>[Cl:64][C:65]1[CH:66]=[CH:67][C:68]([C:71]2[CH:75]=[C:26]([C:24]([NH:23][C:20]3[CH:19]=[CH:18][C:17]([C:12]4[CH:11]=[C:10]5[C:15]([CH2:16][N:8]([C@@H:3]([CH:2]([CH3:1])[CH3:38])[C:4]([O:6][CH3:7])=[O:5])[C:9]5=[O:37])=[CH:14][CH:13]=4)=[CH:22][CH:21]=3)=[O:25])[O:73][N:72]=2)=[CH:69][CH:70]=1

Participants

4

Reactant 3

HCID 776507Ethyl 3-(4-chlorophenyl)isoxazole-5-carboxylateHCID 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 123822721(S)-Methyl 2-(6-(4-(3-(4-chlorophenyl)isoxazole-5-carboxamido)phenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoateYield 48%

Procedure

The compound of example 617 was prepared analogous to the compound of example 611 by reaction of compound of example 6 with ethyl 3-(4-chlorophenyl)isoxazole-5-carboxylate.

Sources & evidence

ORD record
ord-0c414e8680654bdf9f358b83500bb43e
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Reaction notes

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