Water → ethyl 3-(6-aminopyridin-3-yl)-2-[1-(4-[1,2,4]triazol-1-ylbenzyl)-1H-imidazol-4-yl]propionate

HRID 2370938Notes

Reaction equation

HRID 2370938 reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:9]=[CH:8][C:7]([CH2:10][CH:11]([C:17]2[N:18]=[CH:19][NH:20][CH:21]=2)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=1.Br[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH:34]=[N:33][CH:32]=[N:31]2)=[CH:26][CH:25]=1.O>CN(C=O)C>[NH2:3][C:4]1[N:9]=[CH:8][C:7]([CH2:10][CH:11]([C:17]2[N:18]=[CH:19][N:20]([CH2:23][C:24]3[CH:25]=[CH:26][C:27]([N:30]4[CH:34]=[N:33][CH:32]=[N:31]4)=[CH:28][CH:29]=3)[CH:21]=2)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27764891-(4-(bromomethyl)phenyl)-1H-1,2,4-triazoleHCID 178470993HCID 178470993, compound

Product 1

HCID 69331458ethyl 3-(6-aminopyridin-3-yl)-2-[1-(4-[1,2,4]triazol-1-ylbenzyl)-1H-imidazol-4-yl]propionate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

11 mg (0.23 mmol, 50%) of sodium hydride were added to a solution of 60 mg (0.23 mmol) of ethyl 3-(6-aminopyridin-3-yl)-2-(1H-imidazol-4-yl)propionate (example 1g) in 0.5 ml of DMF at RT, and stirred for 1 h. Then 55 mg (0.23 mmol) of 1-[4-(bromomethyl)phenyl]-1H-1,2,4-triazole were added, and the mixture was stirred at RT for 3 h. After this, 1 ml of water was added, the mixture was extracted with EA, and the organic phase was dried over Na2SO4, filtered and concentrated. Chromatography on silica gel afforded ethyl 3-(6-aminopyridin-3-yl)-2-[1-(4-[1,2,4]triazol-1-ylbenzyl)-1H-imidazol-4-yl]propionate. The product obtained in this way was taken up in 0.4 ml of 50% concentrated hydrochloric acid and treated in the microwave at 180° C. for 3 min. Freeze-drying after cooling of the reaction mixture afforded 5 mg of the title compound as bishydrochloride.

Workup

  1. stirringthe mixture was stirred at RT for 3 h
  2. extractionthe mixture was extracted with EA
  3. dry with materialthe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2b025156da9f49d9a8aaa925dbe980a3
Source dataset
uspto-grants-2014_04
Patent number
US08710232B2

Reaction notes

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