4-(Trifluoromethyl)benzoyl chloride → (1S,2R)-Methyl 2-(1-oxo-6-(4-(4-(trifluoromethyl)benzamido)phenyl)isoindolin-2-yl)cyclopentanecarboxylate

HRID 404082Notes

Reaction equation

HRID 404082 reaction equation
C(NC1C=CC(C2C=C3C(CN([C@@H](C(C)C)C(OC)=O)C3=O)=CC=2)=CC=1)(=O)C1C=CC=CC=1.[NH2:34][C:35]1[CH:40]=[CH:39][C:38]([C:41]2[CH:49]=[C:48]3[C:44]([CH2:45][N:46]([C@@H:51]4[CH2:55][CH2:54][CH2:53][C@@H:52]4[C:56]([O:58][CH3:59])=[O:57])[C:47]3=[O:50])=[CH:43][CH:42]=2)=[CH:37][CH:36]=1.[F:60][C:61]([F:72])([F:71])[C:62]1[CH:70]=[CH:69][C:65]([C:66](Cl)=[O:67])=[CH:64][CH:63]=1>>[O:50]=[C:47]1[C:48]2[C:44](=[CH:43][CH:42]=[C:41]([C:38]3[CH:37]=[CH:36][C:35]([NH:34][C:66](=[O:67])[C:65]4[CH:69]=[CH:70][C:62]([C:61]([F:60])([F:71])[F:72])=[CH:63][CH:64]=4)=[CH:40][CH:39]=3)[CH:49]=2)[CH2:45][N:46]1[C@@H:51]1[CH2:55][CH2:54][CH2:53][C@@H:52]1[C:56]([O:58][CH3:59])=[O:57]

Participants

4

Reactant 3

HCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 123625862(S)-Methyl 2-(6-(4-benzamidophenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoateHCID 131731584(1S,2R)-Methyl 2-(6-(4-aminophenyl)-1-oxoisoindolin-2-yl)cyclopentane carboxylate

Product 1

HCID 131731586(1S,2R)-Methyl 2-(1-oxo-6-(4-(4-(trifluoromethyl)benzamido)phenyl)isoindolin-2-yl)cyclopentanecarboxylateYield 86%

Procedure

The compound of example 597 was prepared analogous to compound of example 97 by reaction of compound of example 592 with 4-trifluoromethyl benzoyl chloride.

Sources & evidence

ORD record
ord-210745d55ae244aaaa63027084fef336
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Reaction notes

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