Picolinic acid → N-(3-(2-phenyl-1H-imidazol-1-yl)propyl)picolinamide

HRID 1583995Notes

Reaction equation

HRID 1583995 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[C:22]1([C:28]2[N:29]([CH2:33][CH2:34][CH2:35][NH2:36])[CH:30]=[CH:31][N:32]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCCC1>[C:22]1([C:28]2[N:29]([CH2:33][CH2:34][CH2:35][NH:36][C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[O:9])[CH:30]=[CH:31][N:32]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 1018Picolinic acidHCID 682631,1'-CarbonyldiimidazoleHCID 135889112-phenyl-1H-imidazole-1-propanamine

Product 1

HCID 20257582N-(3-(2-phenyl-1H-imidazol-1-yl)propyl)picolinamideYield 124.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.85 g of picolinic acid and 2.43 g of 1,1'-carbonyldiimidazole in 60 ml of tetrahydrofuran was stirred at room temperature for 2 hours. Then 3.0 g of 2-phenyl-1H-imidazole-1-propanamine was added and the procedure as described in Example 33 was continued to obtain 5.7 g of a viscous oil. The oil was treated by preparative high pressure liquid chromatography using a PrepPAK®-500 Silica column (Waters Associates, Millipore) and ethyl acetate as eluent. Fractions were collected and fractions 5 and 6 were concentrated, treated with ether, and dried and gave 3.8 g of the compound of the Example as an oil.

Sources & evidence

ORD record
ord-e90b4a8177dd47319302d0233f602024
Source dataset
uspto-grants-1985_11
Patent number
US04555519

Reaction notes

Loading…