Triethylamine → HCID 20392921, compound

HRID 1863006Notes

Reaction equation

HRID 1863006 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH:13][C:14]3[CH:27]=[CH:26][C:17]([C:18]([N:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)=[O:19])=[CH:16][CH:15]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.Cl[C:31]1[CH:36]=[N:35][CH:34]=[CH:33][N:32]=1.C(N(CC)CC)C>C(O)CO>[N:32]1[CH:33]=[CH:34][N:35]=[CH:36][C:31]=1[N:23]1[CH2:24][CH2:25][N:20]([C:18](=[O:19])[C:17]2[CH:26]=[CH:27][C:14]([NH:13][C:7]3[C:6]4[C:11](=[CH:12][C:3]([C:2]([F:1])([F:28])[F:29])=[CH:4][CH:5]=4)[N:10]=[CH:9][CH:8]=3)=[CH:15][CH:16]=2)[CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 73277ChloropyrazineHCID 30552431-Piperazinyl(4-((7-(trifluoromethyl)-4-quinolinyl)amino)phenyl)methanone

Product 1

HCID 20392921HCID 20392921, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A mixture of 2.00 g (0.005 mol) of 4-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]piperazine [U.S. Pat. No. 4,025,629] 0.57 g (0.005 mol) of 2-chloropyrazine, and 0.505 g (0.005 mol) of triethylamine is heated in 20 ml of ethylene glycol at 75° C. for 24 hours and at 95° C. for 24 hours. The mixture is partitioned with 1 N toluenesulfonic acid in water and methylene chloride. The aqueous phase is made basic and extracted with methylene chloride. The organic phase is dried with anhydrous sodium sulfate and concentrated. The residue is chromatographed (4% methanol/1/2% ammonium hydroxide/methylene chloride) to yield 0.92 g (38%) of 1-(2-pyrazinyl)-4-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]piperazine. This is re-crystallized from methylene chloride to give 0.48 g of the pure product of melting point 260°-261° C. The IR spectrum is consistent with the named structure.

Workup

  1. customThe mixture is partitioned with 1 N toluenesulfonic acid in water and methylene chloride
  2. extractionextracted with methylene chloride
  3. dry with materialThe organic phase is dried with anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue is chromatographed (4% methanol/1/2% ammonium hydroxide/methylene chloride)

Sources & evidence

ORD record
ord-488fc2fce8c64783a4d0b37776de1655
Source dataset
uspto-grants-1979_09
Patent number
US04167567

Reaction notes

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