Aminopyrazine → HCID 68794299, compound

HRID 237413Notes

Reaction equation

HRID 237413 reaction equation
Cl.[N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][C:13]([OH:15])=O)=[CH:4][CH:3]=1.[NH2:16][C:17]1[CH:22]=[N:21][CH:20]=[CH:19][N:18]=1>CN(C)C=O.N1C=CC=CC=1>[N:18]1[CH:19]=[CH:20][N:21]=[CH:22][C:17]=1[NH:16][C:13](=[O:15])[CH2:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[N:2]=[CH:3][CH:4]=1

Participants

5

Reactant 2

HCID 78747AminopyrazineHCID 17750657HCID 17750657, compound

Product 1

HCID 68794299HCID 68794299, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 200 mg (0.89 mmol) of quinolin-4-yl-acetic acid hydrochloride salt and 145 mg (0.89 mmol) of N,N-carboyl diimidazole was stirred in 3 ml of dimethylformamide at RT for 2 h. 2-Aminopyrazine (63 mg, 0.66 mmol) in 2 ml of pyridine was added dropwise over 10 mins and stirred at 80° C. for a further 9 h. The solution was allowed to cool, concentrated in vacuo, and partitioned between dichloromethane and water. The organic layer was washed 3 times with water, concentrated in vacuo and the material purified by chromatography. White solid. Amount 108 mg. Yield 62%.

Workup

  1. temperatureto cool
  2. concentrationconcentrated in vacuo
  3. custompartitioned between dichloromethane and water
  4. washThe organic layer was washed 3 times with water
  5. concentrationconcentrated in vacuo
  6. customthe material purified by chromatography

Sources & evidence

ORD record
ord-45190d36f5344cb680f9b662572199b1
Source dataset
uspto-grants-2014_02
Patent number
US08642598B2

Reaction notes

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