Triethylamine → N-[1-(2-pyridinyl)-4-piperidinyl]-1H-imidazole-1-carboxamide

HRID 2382339Notes

Reaction equation

HRID 2382339 reaction equation
[CH:1]1[N:5]=[CH:4][N:3]([C:6]([N:8]2C=N[CH:10]=[CH:9]2)=[O:7])[CH:2]=1.C(N(CC)CC)C.Cl.Cl.[N:22]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)[CH2:27]CC(N)[CH2:24][CH2:23]1>C(Cl)Cl>[N:22]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)[CH2:27][CH2:10][CH:9]([NH:8][C:6]([N:3]2[CH:2]=[CH:1][N:5]=[CH:4]2)=[O:7])[CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 666310961-(Pyridin-2-yl)piperidin-4-amine dihydrochloride

Product 1

HCID 21978278N-[1-(2-pyridinyl)-4-piperidinyl]-1H-imidazole-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension comprising CDI (2.29 g, 14 mmol) and triethylamine (3.8 ml, 27 mmol) in dry DCM (20 ml) is treated portionwise over 5 minutes with 3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-ylamine dihydrochloride (prepared using the procedure described in international patent application WO 01/94368) (2.88 g, 13 mmol). The reaction mixture is stirred at room temperature for 4.5 hours to yield the title compound as a 0.43 M solution in DCM.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-a3ad6029801342f2a9d01108e1acc09e
Source dataset
uspto-grants-2012_09
Patent number
US08258141B2

Reaction notes

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