1-Hydroxybenzotriazole → N-[1-[1-(4-bromophenyl)ethyl]-4-piperidinyl]-3-(2-pyridinyl)-1,2,4-oxadiazole-5-propanamide

HRID 1070522Notes

Reaction equation

HRID 1070522 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([N:10]2[CH2:15][CH2:14][CH:13]([NH2:16])[CH2:12][CH2:11]2)[CH3:9])=[CH:4][CH:3]=1.[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[N:27]=[C:26]([CH2:28][CH2:29][C:30](O)=[O:31])[O:25][N:24]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C1C=CN=CC=1)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:10]2[CH2:11][CH2:12][CH:13]([NH:16][C:30](=[O:31])[CH2:29][CH2:28][C:26]3[O:25][N:24]=[C:23]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][N:17]=4)[N:27]=3)[CH2:14][CH2:15]2)[CH3:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 31643283-(3-pyridin-2-yl-1,2,4-oxadiazol-5-yl)propanoic acidHCID 68884300(R)-1-[1-(4-Bromophenyl)ethyl]-4-piperidinamine

Product 1

HCID 22396180N-[1-[1-(4-bromophenyl)ethyl]-4-piperidinyl]-3-(2-pyridinyl)-1,2,4-oxadiazole-5-propanamideYield 5.8%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

Prepared following a method as hereinbefore described using (R)-1-[1-(4-bromophenyl)ethyl]-4-piperidinamine (449 mg), 3-(2-pyridinyl)-1,2,4-oxadiazole-5-propanoic acid (0.31 g), 1-hydroxybenzotriazole (0.20 g), 4-(N,N-dimethylamino)-pyridine (0.13 g) and 1-ethyl-3-[3-(dimethylamino)-propyl]carbodiimide hydrochloride (0.30 g) to give the title compound (40 mg). m.p. 153-155° C.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-a5d5dda308fe41db806242531ccab830
Source dataset
uspto-grants-2005_06
Patent number
US06903085B1

Reaction notes

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