1,1'-Carbonyldiimidazole → N-[1-(2-pyridinyl)-4-piperidinyl]-1H-imidazole-1-carboxamide

HRID 2382340Notes

Reaction equation

HRID 2382340 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.[N:13]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:18]CC(N)[CH2:15][CH2:14]1>C(Cl)Cl>[N:13]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:18][CH2:10][CH:9]([NH:8][C:6]([N:3]2[CH:2]=[CH:1][N:5]=[CH:4]2)=[O:7])[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 101979341-(Pyridin-2-yl)piperidin-4-amine

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution of CDI (1.1 g, 6.77 mmol) in DCM (100 ml) is treated with 3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-ylamine (WO 9965895 EP 21973) (1 g, 5.64 mmol in 50 ml of DCM) added dropwise over 30 minutes. The reaction mixture is stirred at room temperature for 15 minutes to yield the title compound as a 10 mg/ml solution in DCM. The compound is used in solution in subsequent reactions. This solution consists of the imidazole-urea (Intermediate C) together with variable amounts of the corresponding isocyanate and imidazole. This solution is used in the subsequent steps since the imidazole-urea intermediate and isocyanate intermediate are equally suitable as precursors to ureas.

Workup

  1. additionadded dropwise over 30 minutes

Sources & evidence

ORD record
ord-4c45c6ad9d0f4e7faf50884217a0455b
Source dataset
uspto-grants-2012_09
Patent number
US08258141B2

Reaction notes

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