N-{3-[1-(3-aminopropyl)-4-piperidinyl]phenyl}2-methylpropanamide → (4R)-4-(3,4-Difluorophenyl)-N-(3-{4-[3-(isobutyrylamino)phenyl]-1-piperidinyl}propyl)-2-oxo-1,3-oxazolidine-3-carboxamide

HRID 1832723Notes

Reaction equation

HRID 1832723 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[CH2:13][O:12][C:11](=[O:14])[N:10]2[C:15]([O:17]C2C=CC([N+]([O-])=O)=CC=2)=O)[CH:5]=[CH:6][C:7]=1[F:8].[NH2:27][CH2:28][CH2:29][CH2:30][N:31]1[CH2:36][CH2:35][CH:34]([C:37]2[CH:38]=[C:39]([NH:43][C:44](=[O:48])[CH:45]([CH3:47])[CH3:46])[CH:40]=[CH:41][CH:42]=2)[CH2:33][CH2:32]1>>[F:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[CH2:13][O:12][C:11](=[O:14])[N:10]2[C:15]([NH:27][CH2:28][CH2:29][CH2:30][N:31]2[CH2:36][CH2:35][CH:34]([C:37]3[CH:42]=[CH:41][CH:40]=[C:39]([NH:43][C:44](=[O:48])[CH:45]([CH3:46])[CH3:47])[CH:38]=3)[CH2:33][CH2:32]2)=[O:17])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

3

Reactant 2

HCID 16757470N-{3-[1-(3-aminopropyl)-4-piperidinyl]phenyl}2-methylpropanamideHCID 600786674-nitrophenyl(4R)-4-(3,4-difluorophenyl)-2-oxo-1,3-oxazolidine-3-carboxylate

Product 1

HCID 60078683(4R)-4-(3,4-Difluorophenyl)-N-(3-{4-[3-(isobutyrylamino)phenyl]-1-piperidinyl}propyl)-2-oxo-1,3-oxazolidine-3-carboxamide

Procedure

Prepared by Procedure AF and Scheme H using 4-nitrophenyl (4R)-4-(3,4-difluorophenyl)-2-oxo-1,3-oxazolidine-3-carboxylate and N-{3-[1-(3-aminopropyl)-4-piperidinyl]phenyl}-2-methylpropanamide: 1H NMR (400 MHz, CDCl3) δ 8.08 (t, 1H, J=5.5 Hz), 7.45 (S, 2H), 7.38 (d, 1H, J=8.6 Hz), 7.24–7.12 (m, 3H), 7.06 (m, 1H), 6.97 (d, 1H, J=8.6 Hz), 5.40 (dd, 1H, J=3.9, 8.8 Hz), 4.71 (t, 1H, J=8.8 Hz), 4.23 (dd, 1H, J=4.4, 9.1 Hz), 3.32 (qt, 2H, J=6.1 Hz), 2.99 (d, 2H, J=11.0 Hz), 2.49 (qt, 2H, J=7.0 Hz), 2.41 (t, 2H, J=7.0 Hz), 1.99 (m, 2H), 1.82–1.68 (m, 6H), 1.23 (d, 6H, J=7.3 Hz); ESMS m/e: 529.1 (M+H)+.

Workup

  1. customPrepared by Procedure AF and Scheme H

Sources & evidence

ORD record
ord-c41250d8bd2044f3b017bd85bbfc4c1c
Source dataset
uspto-grants-2006_06
Patent number
US07067534B1

Reaction notes

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