Sodium Bicarbonate → 6-(8-Chloropyrido[2,3-b]pyrazin-3-yl)-5-(trifluoromethyl)nicotinamide

HRID 545094Notes

Reaction equation

HRID 545094 reaction equation
O[CH:2](O)[C:3]([C:5]1[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][C:8]([C:9]([NH2:11])=[O:10])=[CH:7][N:6]=1)=O.[Cl:19][C:20]1[CH:25]=[CH:24][N:23]=[C:22]([NH2:26])[C:21]=1[NH2:27].C([O-])(O)=O.[Na+]>CCO>[Cl:19][C:20]1[C:21]2[C:22](=[N:26][C:3]([C:5]3[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][C:8]([C:9]([NH2:11])=[O:10])=[CH:7][N:6]=3)=[CH:2][N:27]=2)[N:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 224180044-Chloropyridine-2,3-diamineHCID 671896796-(2,2-Dihydroxyacetyl)-5-(trifluoromethyl)nicotinamide

Product 1

HCID 671914016-(8-Chloropyrido[2,3-b]pyrazin-3-yl)-5-(trifluoromethyl)nicotinamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolve 6-(2,2-dihydroxyacetyl)-5-(trifluoromethyl)nicotinamide (8.0 g) in 100.0 mL of EtOH and then add 4-chloro-2,3-diaminopyridine (800 mg) followed by addition of NaHCO3 (3.6 g). Stir the reaction at room temperature for 18 hours under N2 atmosphere. Concentrate the reaction mixture under vacuum, and purify by column chromatography to afford the title product as a yellow solid.

Workup

  1. customthe reaction at room temperature for 18 hours under N2 atmosphere
  2. concentrationConcentrate the reaction mixture under vacuum
  3. custompurify by column chromatography

Sources & evidence

ORD record
ord-5cc52d70bbfa4d979ed3c1009b47bef5
Source dataset
uspto-grants-2011_05
Patent number
US07935702B2

Reaction notes

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