Water → HCID 86598206, compound

HRID 2217225Notes

Reaction equation

HRID 2217225 reaction equation
[NH2:1][C:2]1[C:3]([C:17]([NH2:19])=[O:18])=[N:4][C:5]([C:9]2[CH:14]=[CH:13][C:12](=[O:15])[N:11]([CH3:16])[CH:10]=2)=[CH:6][N+:7]=1[O-].P(Cl)(Cl)([Cl:22])=O.O.[OH-].[Na+]>CN(C=O)C>[NH2:1][C:2]1[C:3]([C:17]([NH2:19])=[O:18])=[N:4][C:5]([C:9]2[CH:14]=[CH:13][C:12](=[O:15])[N:11]([CH3:16])[CH:10]=2)=[C:6]([Cl:22])[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 178480107HCID 178480107, compound

Product 1

HCID 86598206HCID 86598206, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-10 °C

Procedure

To a suspension of 3-amino-6-(1-methyl-6-oxo-1,6-dihydro-3-pyridyl)-2-pyrazinecarboxamide 4-oxide (1.0 g) in DMF was added phosphoric trichloride (1.07 ml) at −40° C. for 20 minutes. This reaction mixture was warmed to −10° C. and stirred for 1 hour. To this solution was added water (40 ml) and stirred at 40° C. for 14 hours. The pH of the resulting suspension was adjusted to 4.5 with 30% The pH of the aqueous mixture was adjusted to 6-7 with 12% aq. NaOH. The precipitate was collected by filtration and washed with water to give 3-amino-5-chloro-6-(1-methyl-6-oxo-1,6-dihydro-3-pyridyl)-2-pyrazinecarboxamide (263 mg) as a yellow powder.

Workup

  1. stirringstirred at 40° C. for 14 hours
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-69ff969bbc0c48dba6951bcad322582c
Source dataset
uspto-grants-2008_08
Patent number
US07407961B2

Reaction notes

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