Sodium hydride → HCID 52948089, compound

HRID 633289Notes

Reaction equation

HRID 633289 reaction equation
[CH3:1][C:2]1[N:6]=[CH:5][NH:4][N:3]=1.[H-].[Na+].Cl[C:10]1[CH:31]=[CH:30][C:13]([C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)[CH:18]=2)=[O:15])=[C:12]([CH3:32])[N:11]=1>CN(C=O)C>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([NH:16][C:14](=[O:15])[C:13]2[CH:30]=[CH:31][C:10]([N:4]3[CH:5]=[N:6][C:2]([CH3:1])=[N:3]3)=[N:11][C:12]=2[CH3:32])=[CH:18][C:19]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 586147986-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)-2-methylnicotinamideHCID 178433329HCID 178433329, compound

Product 1

HCID 52948089HCID 52948089, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 57 mg of 3-methyl-1,2,4-triazol and 16 mg of sodium hydride in 2 mL of DMF was stirred for 10 min. 80 mg of 6-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)-2-methylnicotinamide was added. The reaction was heated to 140° C. for 16 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-(3-methyl-1H-1,2,4-triazol-1-yl)nicotinamide. MS (Q1) 405.3 (M)+.

Workup

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

Sources & evidence

ORD record
ord-fc9b833ad5204ed496b323581ba1f868
Source dataset
uspto-grants-2016_04
Patent number
US09321761B2

Reaction notes

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