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

HRID 2099276Notes

Reaction equation

HRID 2099276 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 57794728N-{[(1S,2R)-2-formyl-1-phenylcyclopropyl]methyl}-N-methylbenzenesulfonamide

Product 1

HCID 9985186N-[((1S,2R)-2-{[4-(3-benzyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl]methyl}-1-phenylcyclopropyl)methyl]-N-methylbenzenesulfonamide

Procedure

N-{[(1S,2R)-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-d6) δ 7.69-7.55 (m, 5H), 7.36-7.18 (m, 10H), 4.08 (s, 2H), 3.91 (d, J=13.2 Hz, 1H), 3.08-2.98 (m, 2H), 2.81 (d, J=13.2 Hz, 1H), 2.84-2.78 (m, 1H), 2.59-2.43 (m, 2H), 2.52 (s, 3H), 2.27-1.97 (m, 4H), 1.80-1.66 (m, 2H), 1.45-1.39 (m, 1H), 1.09-0.99 (m, 1H), 0.80 (m, 1H). ES-LCMS m/z 557.2 (M+H).

Sources & evidence

ORD record
ord-77ce63e5bdf24226a96fe650cbe9b3af
Source dataset
uspto-grants-2009_08
Patent number
US07569579B2

Reaction notes

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