3,3-Diphenylpyrrolidine → 1-[2-(5-fluoro-1,3-dihydro-2H-isoindol-2-yl)-2-oxoethyl]-3-[4-(trifluoromethyl)phenyl]pyrrolidin-2-one

HRID 1667294

Reaction equation

HRID 1667294 reaction equation
[O:1]=[C:2]1[CH:6]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)[CH2:5][CH2:4][N:3]1[CH2:17][C:18](O)=[O:19].FC1C=CC(C2(C3C=CC(F)=CC=3)CCCN(CC(O)=O)C2=O)=CC=1.[F:46][C:47]1[CH:48]=[C:49]2[C:53](=[CH:54][CH:55]=1)[CH2:52][NH:51][CH2:50]2.C1(C2(C3C=CC=CC=3)CCNC2)C=CC=CC=1>>[F:46][C:47]1[CH:48]=[C:49]2[C:53](=[CH:54][CH:55]=1)[CH2:52][N:51]([C:18](=[O:19])[CH2:17][N:3]1[CH2:4][CH2:5][CH:6]([C:7]3[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=3)[C:2]1=[O:1])[CH2:50]2

Participants

5

Reactant 4

HCID 4182423,3-DiphenylpyrrolidineHCID 147958695-Fluoro-2,3-dihydro-1H-isoindoleHCID 67358165HCID 67358165, compoundHCID 673591112-(3,3-Bis(4-fluorophenyl)-2-oxopiperidin-1-yl)acetic acid

Product 1

HCID 673586321-[2-(5-fluoro-1,3-dihydro-2H-isoindol-2-yl)-2-oxoethyl]-3-[4-(trifluoromethyl)phenyl]pyrrolidin-2-one

Procedure

The title compound was prepared using the procedure described in Example 172 substituting 2-(2-oxo-3-(4-(trifluoromethyl)phenyl)pyrrolidin-1-yl)acetic acid from Example 266D for 2-(3,3-bis(4-fluorophenyl)-2-oxopiperidin-1-yl)acetic acid and 5-fluoroisoindoline for 3,3-diphenylpyrrolidine. 1H NMR (300 MHz, CDCl3) δ ppm 7.61 (d, J=8.2, 2H), 7.46 (d, J=8.2, 2H), 7.32-7.16 (m, 1H), 7.06-6.89 (m, 2H), 4.82 (dd, J=8.7, 15.1, 4H), 4.34-4.13 (m, 2H), 3.83 (t, J=8.9, 1H), 3.77-3.60 (m, 2H), 2.72-2.53 (m, 1H), 2.22 (ddd, J=8.5, 12.9, 16.1, 1H); MS (DCI) m/z 407.1 (M+H)+.

Sources & evidence

ORD record
ord-6ff5c63c1fe745e29f23249f0d4e8af4
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Linked notes

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