Triethylamine → HCID 13544851, compound

HRID 1863008Notes

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.[NH2:30][C:31]1[N:36]=[C:35](Cl)[CH:34]=[C:33]([CH3:38])[N:32]=1.C(N(CC)CC)C.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.C(O)CO>[NH2:30][C:31]1[N:36]=[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:34]=[C:33]([CH3:38])[N:32]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4.00 g (0.010 mol) of 4-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]piperazine, 1.43 g (0.010 mol) of 2-amino-4-chloro-6-methylpyrimidine, 1.39 ml (0.01 mol) of triethylamine, and 125 ml of ethylene glycol is stirred at 100° C. for 5 hours. The reaction mixture is shaken with aqueous sodium carbonate and methylene chloride and the remaining solid is then collected by filtration. The product, 1-(2-amino-6-methyl-4-pyrimidinyl)-4-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]piperazine (4.06 g, 80%), is crystallized twice from methanol/methylene chloride; it has a melting point of 283°-286° C.

Workup

filtrationthe remaining solid is then collected by filtration
customThe product, 1-(2-amino-6-methyl-4-pyrimidinyl)-4-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]piperazine (4.06 g, 80%), is crystallized twice from methanol/methylene chloride

Sources & evidence

ORD record: ord-54ca82eac8474a9c9c257a9ee9cb3bea
Source dataset: uspto-grants-1979_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04167567

Reaction notes

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