2-Chloro-4-fluorobenzylamine → N-{[4-fluoro-2-(trifluoromethyl)phenyl]methyl}-1-methyl-5-oxoprolinamide

HRID 2238516Notes

Reaction equation

HRID 2238516 reaction equation
Cl[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][NH:10][C:11](=[O:20])[C@@H:12]1[CH2:16][CH2:15][C:14](=[O:17])[N:13]1[CH2:18]C.CN1C(=O)CC[C@H]1C(O)=O.C(N1C(=O)CC[C@H]1C(O)=O)C.FC1C=CC(CN)=C([C:51]([F:54])([F:53])[F:52])C=1.ClC1C=C(F)C=CC=1CN>>[F:8][C:6]1[CH:5]=[CH:4][C:3]([CH2:9][NH:10][C:11](=[O:20])[C@@H:12]2[CH2:16][CH2:15][C:14](=[O:17])[N:13]2[CH3:18])=[C:2]([C:51]([F:54])([F:53])[F:52])[CH:7]=1

Participants

6

Reactant 5

HCID 1399092-Chloro-4-fluorobenzylamineHCID 2734878(4-Fluoro-2-(trifluoromethyl)phenyl)methanamineHCID 18605196L-Proline, 1-ethyl-5-oxo-HCID 18649403(2S)-1-methyl-5-oxopyrrolidine-2-carboxylic acidHCID 49864911N-[(2-chloro-4-fluorophenyl)methyl]-1-ethyl-5-oxoprolinamide

Product 1

HCID 67458706N-{[4-fluoro-2-(trifluoromethyl)phenyl]methyl}-1-methyl-5-oxoprolinamide

Procedure

N-{[4-fluoro-2-(trifluoromethyl)phenyl]methyl}-1-methyl-5-oxoprolinamide was prepared in a manner analogous to that described above for the synthesis of N-[(2-chloro-4-fluorophenyl)methyl]-1-ethyl-5-oxoprolinamide (Example 70) but 1-methyl-5-oxoproline (prepared as describe below) was substituted for 1-ethyl-5-oxoproline and {[4-fluoro-2-(trifluoromethyl)phenyl]methyl}amine was substituted for 2-chloro-4-fluorobenzylamine.

Sources & evidence

ORD record
ord-ef671c41249e47279a1622cd1c4b4945
Source dataset
uspto-grants-2010_05
Patent number
US07718693B2

Reaction notes

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