N'-Hydroxy-4-(trifluoromethyl)benzene-1-carboximidamide → 1-{[3-(4-Methylphenyl)-1,2,4-oxadiazol-5-yl]methyl}-3,3-diphenylpyrrolidin-2-one

HRID 1667234Notes

Reaction equation

HRID 1667234 reaction equation
[O:1]=[C:2]1[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4][N:3]1[CH2:19][C:20]([OH:22])=O.FC1C=CC(C2(C3C=CC(F)=CC=3)CCN(CC(O)=O)C2=O)=CC=1.O[NH:48]/[C:49](=[N:57]\[H])/[C:50]1[CH:55]=[CH:54][C:53]([CH3:56])=[CH:52][CH:51]=1.ON/C(=N\[H])/C1C=CC(C(F)(F)F)=CC=1>>[CH3:56][C:53]1[CH:54]=[CH:55][C:50]([C:49]2[N:57]=[C:20]([CH2:19][N:3]3[CH2:4][CH2:5][C:6]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=4)[C:2]3=[O:1])[O:22][N:48]=2)=[CH:51][CH:52]=1

Participants

5

Reactant 4

HCID 609329N'-Hydroxy-4-(trifluoromethyl)benzene-1-carboximidamideHCID 673571912-(3,3-Bis(4-fluorophenyl)-2-oxopyrrolidin-1-yl)acetic acidHCID 673590132-(2-Oxo-3,3-diphenylpyrrolidin-1-yl)acetic acidHCID 178506494HCID 178506494, compound

Product 1

HCID 452748181-{[3-(4-Methylphenyl)-1,2,4-oxadiazol-5-yl]methyl}-3,3-diphenylpyrrolidin-2-one

Procedure

The title compound was prepared using the procedure described in Example 190 substituting 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid from Example 1C for 2-(3,3-bis(4-fluorophenyl)-2-oxopyrrolidin-1-yl)acetic acid and (Z)—N-hydroxy-4-methylbenzimidamide for (Z)—N-hydroxy-4-(trifluoromethyl)benzimidamide. 1H NMR (300 MHz, CDCl3) δ ppm 7.93-7.87 (m, 2H), 7.43-7.22 (m, 10H), 7.08 (s, 1H), 6.90-6.81 (m, 1H), 4.88 (s, 2H), 3.56 (t, J=6.5, 2H), 2.88 (t, J=6.5, 2H), 2.42 (s, 3H)); MS (DCI) m/z 410.1 (M+H)+.

Sources & evidence

ORD record
ord-71e26c69db564d3095fcaff288112d78
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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