Triethylamine → HCID 13544850, compound

HRID 1863010Notes

Reaction equation

HRID 1863010 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]=[CH:35][N:34]=[C:33]([S:37][CH3:38])[N:32]=1.C(N(CC)CC)C>C(O)C>[CH3:38][S:37][C:33]1[N:34]=[C:35]([N:23]2[CH2:24][CH2:25][N:20]([C:18](=[O:19])[C:17]3[CH:26]=[CH:27][C:14]([NH:13][C:7]4[C:6]5[C:11](=[CH:12][C:3]([C:2]([F:1])([F:28])[F:29])=[CH:4][CH:5]=5)[N:10]=[CH:9][CH:8]=4)=[CH:15][CH:16]=3)[CH2:21][CH2:22]2)[CH:36]=[CH:31][N:32]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 971134-Chloro-2-methylthiopyrimidineHCID 30552431-Piperazinyl(4-((7-(trifluoromethyl)-4-quinolinyl)amino)phenyl)methanone

Product 1

HCID 13544850HCID 13544850, compoundYield 26.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.50 g (0.0037 mol) of 4-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]piperazine [U.S. Pat. No. 4,025,629], 0.44 ml (0.00375 mol) of 4-chloro-2-methylthiopyrimidine, 0.52 ml (0.00375 mol) of triethylamine, and 125 ml of ethanol is stirred at reflux for 3 hours. After cooling, the ethanol is removed in vacuo and the residue is stirred with methylene chloride and aqueous sodium bicarbonate. The resultant solid is collected and washed with water and ether. Crystallization from methanol-chloroform gives 0.52 g (26%) of 1-[2-(methylthio)-4-pyrimidinyl]-4-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]piperazine, of melting point 166°-267° C.

Workup

  1. temperatureat reflux for 3 hours
  2. temperatureAfter cooling
  3. customthe ethanol is removed in vacuo
  4. customThe resultant solid is collected
  5. washwashed with water and ether
  6. customCrystallization from methanol-chloroform

Sources & evidence

ORD record
ord-dedc21b8eed34e128e56795b9a8b0b05
Source dataset
uspto-grants-1979_09
Patent number
US04167567

Reaction notes

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