Triethylamine → [4-(2,6-Dimethoxypyrimidin-4-yl)piperazin-1-yl](4-{[7-(trifluoromethyl)quinolin-4-yl]amino}phenyl)methanone

HRID 1863009Notes

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[N:36]=[C:35]([O:37][CH3:38])[N:34]=[C:33]([O:39][CH3:40])[CH:32]=1.C(N(CC)CC)C>C(O)CO>[CH3:38][O:37][C:35]1[N:36]=[C:31]([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:32]=[C:33]([O:39][CH3:40])[N:34]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3.70 g (0.00924 mol) of 4-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]piperazine, 1.61 g (0.00924 mol) of 6-chloro-2,4-dimethoxypyrimidine, 1.29 ml (0.00924 mol) of triethylamine and 125 ml of ethylene glycol is heated at 100° C. for 6 hours. After cooling, the precipitated solid is collected on a sintered glass funnel and dried in the air over the weekend. The solid is chromatographed on silica gel, eluting with 6% methanol/methylene chloride, to give 2.15 g (43%) of 1-(2,6-dimethoxy-4-pyrimidinyl)-4-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]piperazine of melting point 260°-262° C., after crystallization from methanol/methylene chloride.

Workup

temperatureAfter cooling
customthe precipitated solid is collected on a sintered glass funnel
customdried in the air over the weekend
customThe solid is chromatographed on silica gel
washeluting with 6% methanol/methylene chloride

Sources & evidence

ORD record: ord-057f8937ff0241c9819e9c9287e44fc8
Source dataset: uspto-grants-1979_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04167567

Reaction notes

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