Oxalyl chloride → HCID 57799151, compound

HRID 2100348Notes

Reaction equation

HRID 2100348 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][N:8]1[C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=[N:9]1.[Cl:16][C:17]1[C:18]([NH2:24])=[N:19][C:20]([NH2:23])=[CH:21][N:22]=1>ClCCl.CN(C)C=O>[NH2:24][C:18]1[N:19]=[C:20]([NH:23][C:13]([C:12]2[N:8]([CH3:7])[N:9]=[CH:10][CH:11]=2)=[O:15])[CH:21]=[N:22][C:17]=1[Cl:16]

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 6431581-methyl-1H-pyrazole-5-carboxylic acidHCID 121014923-Chloropyrazine-2,6-diamine

Product 1

HCID 57799151HCID 57799151, compoundYield 35.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (0.288 ml, 3.32 mmol) was added to a suspension of 1-methyl-1H-pyrazole-5-carboxylic acid (0.279 g, 2.21 mmol) in dichloromethane (5 ml) followed by 1 drop of dimethylformamide. The mixture was stirred at room temperature for 4 hours before concentrating in vacuo and azeotroping with dichloromethane. The residue was taken up in pyridine (1 ml) and added to a solution of 3-chloro-pyrazine-2,6-diamine (Preparation 1) (0.16 g, 1.11 mmol) and the mixture heated at 60° C. for 3 hours before cooling to room temperature and concentrating in vacuo. The residue was purified by silica gel column chromatography, eluting with ethylacetate:heptane 1:1, to afford the product as a pale solid (100 mg).

Workup

  1. concentrationbefore concentrating in vacuo
  2. customazeotroping with dichloromethane
  3. temperaturethe mixture heated at 60° C. for 3 hours
  4. temperaturebefore cooling to room temperature
  5. concentrationconcentrating in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with ethylacetate:heptane 1:1

Sources & evidence

ORD record
ord-9556d7f98ff5494b93ee7fa2fd9ed7d8
Source dataset
uspto-grants-2009_08
Patent number
US07572797B2

Reaction notes

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