Triethylamine → 4-(2-Pyrimidinyl)-1-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]piperazine

HRID 1863007Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[F:8][C:9]([F:36])([F:35])[C:10]1[CH:19]=[C:18]2[C:13]([C:14]([NH:20][C:21]3[CH:34]=[CH:33][C:24]([C:25]([N:27]4[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]4)=[O:26])=[CH:23][CH:22]=3)=[CH:15][CH:16]=[N:17]2)=[CH:12][CH:11]=1.C(N(CC)CC)C>C(O)C>[N:3]1[CH:4]=[CH:5][CH:6]=[N:7][C:2]=1[N:30]1[CH2:31][CH2:32][N:27]([C:25](=[O:26])[C:24]2[CH:23]=[CH:22][C:21]([NH:20][C:14]3[C:13]4[C:18](=[CH:19][C:10]([C:9]([F:8])([F:35])[F:36])=[CH:11][CH:12]=4)[N:17]=[CH:16][CH:15]=3)=[CH:34][CH:33]=2)[CH2:28][CH2:29]1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 1.30 g (0.0114 mol) of 2-chloropyrimidine, 3.50 g (0.00875 mol) of 1-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]piperazine, and 1.2 g of triethylamine in 50 ml of ethanol is stirred at 50° C. for 15 hours and at reflux for 8 hours. The mixture is partitioned between methylene chloride and aqueous 1 N sodium hydroxide. The organic phase is dried and concentrated. The residue is re-crystallized from methylene chloride and ethanol to yield 4.00 g of 4-(2-pyrimidinyl)-1-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]piperazine, of melting point 246°-247.5° C.

Workup

temperatureat reflux for 8 hours
customThe mixture is partitioned between methylene chloride and aqueous 1 N sodium hydroxide
customThe organic phase is dried
concentrationconcentrated
customThe residue is re-crystallized from methylene chloride and ethanol

Sources & evidence

ORD record: ord-9afb6bbb77f44cff9e0a68960f4545a1
Source dataset: uspto-grants-1979_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04167567

Reaction notes

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