1H-1,2,4-Triazole → HCID 58614635, compound

HRID 1364915Notes

Reaction equation

HRID 1364915 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[H-].[Na+].Cl[C:9]1[CH:30]=[CH:29][C:12]([C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[CH:17]=2)=[O:14])=[C:11]([CH3:31])[N:10]=1>CN(C=O)C>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([NH:15][C:13](=[O:14])[C:12]2[CH:29]=[CH:30][C:9]([N:1]3[CH:5]=[N:4][CH:3]=[N:2]3)=[N:10][C:11]=2[CH3:31])=[CH:17][C:18]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 586147986-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)-2-methylnicotinamide

Product 1

HCID 58614635HCID 58614635, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 41 mg of 1,2,4-triazol and 14 mg of sodium hydride in 2 mL of DMF was stirred for 10 min. 70 mg of 6-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)-2-methylnicotinamide was added. The reaction was heated to 140° C. for 6 h. The reaction mixture was quenched with MeOH and evaporated. Purified by reverse phase HPLC to yield N-(4-chloro-3-(pyridin-2-yl)phenyl)-2-methyl-6-(1H-1,2,4-triazol-1-yl)nicotinamide. MS (Q1) 391.4 (M)+.

Workup

  1. customThe reaction mixture was quenched with MeOH
  2. customevaporated
  3. customPurified by reverse phase HPLC

Sources & evidence

ORD record
ord-12be25091f6245c5a841bed3bf99b755
Source dataset
uspto-grants-2011_02
Patent number
US07888364B2

Reaction notes

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