4-(3-Benzyl-1,2,4-oxadiazol-5-yl)piperidine → N-[((1S,2S)-2-{[4-(3-benzyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl]methyl}-1-phenylcyclopropyl)methyl]-N-methylbenzenesulfonamide

HRID 2099278Notes

Reaction equation

HRID 2099278 reaction equation
[CH:1]([C@H:3]1[CH2:5][C@@:4]1([CH2:12][N:13]([CH3:23])[S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.[CH2:24]([C:31]1[N:35]=[C:34]([CH:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)[O:33][N:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[CH2:24]([C:31]1[N:35]=[C:34]([CH:36]2[CH2:41][CH2:40][N:39]([CH2:1][C@H:3]3[CH2:5][C@@:4]3([CH2:12][N:13]([CH3:23])[S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)(=[O:16])=[O:15])[C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:38][CH2:37]2)[O:33][N:32]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

3

Reactant 2

HCID 415417574-(3-Benzyl-1,2,4-oxadiazol-5-yl)piperidineHCID 57794803N-{[(1S,2S)-2-formyl-1-phenylcyclopropyl]methyl}-N-methylbenzenesulfonamide

Product 1

HCID 57794726N-[((1S,2S)-2-{[4-(3-benzyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl]methyl}-1-phenylcyclopropyl)methyl]-N-methylbenzenesulfonamide

Procedure

N-{[(1S,2S)-2-formyl-1-phenylcyclopropyl]methyl}-N-methylbenzenesulfonamide and 4-(3-benzyl-1,2,4-oxadiazol-5-yl)piperidine (incorporating by reference as needed WO 00/39125) were reacted as per Preparation 10 to give the title compound. 1H NMR (300 MHz, DMSO-de) δ 7.69-7.54 (m, 5H), 7.35-7.20 (m, 10H), 4.06 (s, 2H), 3.55 (d, J=13.8 Hz, 1H), 2.97-2.85 (m, 1H), 2.78 (d, J=13.8 Hz, 1H), 2.64-2.59 (m, 1H), 2.53 (s, 3H), 2.27-2.21 (m, 1H), 2.02-1.88 (m, 4H), 1.75-1.61 (m, 2H), 1.48-1.41 (m, 1H), 1.17 (m, 1H), 1.07-1.02 (m, 1H), 0.93-0.89 (m, 1H). ES-LCMS m/z 557.1 (M+H).

Sources & evidence

ORD record
ord-de8ed38457d54c9e8be1d65a3c10692d
Source dataset
uspto-grants-2009_08
Patent number
US07569579B2

Reaction notes

Loading…