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

HRID 1667296Notes

Reaction equation

HRID 1667296 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]([OH:17])=O)[C:10]1=[O:18].FC1C=CC(C2(C3C=CC(F)=CC=3)CCCN(CC(O)=O)C2=O)=CC=1.[F:44][C:45]1[CH:46]=[C:47]2[C:51](=[CH:52][CH:53]=1)[CH2:50][NH:49][CH2:48]2.C1(C2(C3C=CC=CC=3)CCNC2)C=CC=CC=1>>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]([N:49]2[CH2:48][C:47]3[C:51](=[CH:52][CH:53]=[C:45]([F:44])[CH:46]=3)[CH2:50]2)=[O:17])[C:10]1=[O:18]

Participants

5

Reactant 4

HCID 4182423,3-DiphenylpyrrolidineHCID 147958695-Fluoro-2,3-dihydro-1H-isoindoleHCID 673591112-(3,3-Bis(4-fluorophenyl)-2-oxopiperidin-1-yl)acetic acidHCID 673604082-(3-(2-Chloro-4-fluorophenyl)-2-oxopyrrolidin-1-yl)acetic acid

Product 1

HCID 452745083-(2-chloro-4-fluorophenyl)-1-[2-(5-fluoro-1,3-dihydro-2H-isoindol-2-yl)-2-oxoethyl]pyrrolidin-2-one

Procedure

The title compound was prepared using the procedure described in Example 172 substituting 2-(3-(2-chloro-4-fluorophenyl)-2-oxopyrrolidin-1-yl)acetic acid from Example 268A 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 7.36 (dd, J=6.0, 8.7, 1H), 7.28-7.17 (m, 1H), 7.17-7.12 (m, 1H), 7.09-6.91 (m, 3H), 4.84 (dd, J=8.5, 17.8, 4H), 4.34 (d, J=8.0, 1H), 4.24-4.07 (m, 2H), 3.77-3.56 (m, 2H), 2.76-2.55 (m, 1H), 2.03 (ddd, J=8.6, 12.8, 16.4, 1H); MS (DCI) m/z 391.1 (M+H)+.

Sources & evidence

ORD record
ord-54654be3af494704b8308b33d378c7f6
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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