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Sodium Hydroxide → HCID 86600909, compound

HRID 915019
Notes
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Reaction equation

HRID 915019 reaction equation
[NH2:1][C:2]1[C:3]([C:19]([NH2:21])=[O:20])=[N:4][C:5]([C:9]2[CH:14]=[CH:13][C:12](=[O:15])[N:11]([CH:16]([CH3:18])[CH3:17])[N:10]=2)=[CH:6][N+:7]=1[O-].[OH-].[Na+].P(Cl)(Cl)([Cl:26])=O>CN(C=O)C>[NH2:1][C:2]1[C:3]([C:19]([NH2:21])=[O:20])=[N:4][C:5]([C:9]2[CH:14]=[CH:13][C:12](=[O:15])[N:11]([CH:16]([CH3:18])[CH3:17])[N:10]=2)=[C:6]([Cl:26])[N:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 178456630HCID 178456630, compound

Product 1

HCID 86600909HCID 86600909, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
2.5 °C

Procedure

To a suspension 3-amino-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-pyrazinecarboxamide 4-oxide (1.65 g) in DMF (33 ml), phosphorous oxychloride (1.59 ml) was added below −30° C. and the mixture was stirred at 0-5° C. for one hour. The reaction mixture was poured into ice-water (132 ml), stirred at 40-50° C. for 2 hours, adjusted to pH 8 with 30% aq. NaOH solution under ice-cooling and a precipitate was collected by filtration. The precipitate was purified by column chromatography on silica gel eluting with a mixture of MeOH and EtOAc (2:98 v/v) to give 3-amino-5-chloro-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-pyrazinecarboxamide as a solid (682 mg).

Workup

  1. stirringstirred at 40-50° C. for 2 hours
  2. temperaturecooling
  3. filtrationa precipitate was collected by filtration
  4. customThe precipitate was purified by column chromatography on silica gel eluting with a mixture of MeOH and EtOAc (2:98 v/v)

Sources & evidence

ORD record
ord-fc43b84bdb5748c5bac854fd43d5fbca
Source dataset
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07265120B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes