1,1'-Carbonyldiimidazole → HCID 66736778, compound

HRID 1696970Notes

Reaction equation

HRID 1696970 reaction equation
Cl.Cl.[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:13][CH2:12][C@H:11]([NH2:14])[CH2:10]1.[CH:15]1[N:19]=[CH:18][N:17]([C:20](N2C=NC=C2)=[O:21])[CH:16]=1>C(Cl)Cl>[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:13][CH2:12][C@H:11]([NH:14][C:20]([N:17]2[CH:16]=[CH:15][N:19]=[CH:18]2)=[O:21])[CH2:10]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 67019379(3S)-1-(pyridin-2-yl)pyrrolidin-3-amine dihydrochloride

Product 1

HCID 66736778HCID 66736778, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture comprising ((S)-1-Pyridin-2-yl-pyrrolidin-3-ylamine dihydrochloride (0.242 g, 1.02 mmol), TEA (0.2 ml) in DCM (10.2 ml) is treated with CDI (0.364 g, 2.26 mmol). The reaction mixture is stirred at room temperature for 2 hours to yield the titled compound as 0.1 M solution in DCM. This solution consists of the imidazole-urea intermediate 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.

Sources & evidence

ORD record
ord-eef5d918534543ff83f9e9c4eca9d560
Source dataset
uspto-grants-2012_04
Patent number
US08163754B2

Reaction notes

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