Ethyl 3-(4-(trifluoromethyl)phenyl)isoxazole-5-carboxylate → (S)-Methyl 3-methyl-2-(1-oxo-6-(4-(3-(4-(trifluoromethyl)phenyl)isoxazole-5-carboxamido)phenyl)isoindolin-2-yl)butanoate

HRID 404095Notes

Reaction equation

HRID 404095 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.[F:64][C:65]([F:83])([F:82])[C:66]1[CH:71]=[CH:70][C:69]([C:72]2[CH:76]=C(C(OCC)=O)[O:74][N:73]=2)=[CH:68][CH:67]=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:22]=[CH:21][C:20]([NH:23][C:24]([C:26]4[O:74][N:73]=[C:72]([C:69]5[CH:70]=[CH:71][C:66]([C:65]([F:64])([F:82])[F:83])=[CH:67][CH:68]=5)[CH:76]=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]

Participants

4

Reactant 3

HCID 67282580Ethyl 3-(4-(trifluoromethyl)phenyl)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 123681234(S)-Methyl 3-methyl-2-(1-oxo-6-(4-(3-(4-(trifluoromethyl)phenyl)isoxazole-5-carboxamido)phenyl)isoindolin-2-yl)butanoateYield 62%

Procedure

The compound of example 619 was prepared analogous to the compound of example 611 by reaction of compound of example 6 with ethyl 3-(4-(trifluoromethyl)phenyl)isoxazole-5-carboxylate.

Sources & evidence

ORD record
ord-8086f1cac21e499db9b9c926688c9e6f
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Reaction notes

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