Dimethylformamide → 3-{4-[(4-Chlorobenzyl)oxy]benzyl}-6-[4-(4-fluorophenyl)piperazin-1-yl]-1,3,5-triazine-2,4(1H,3H)-dione
Reaction equation
CN(C)C=O.[F:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[NH:24][C:23](=[O:25])[NH:22][C:21](=[O:26])[N:20]=3)[CH2:15][CH2:14]2)=[CH:9][CH:8]=1.[H-].[Li+].[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][O:37][C:38]2[CH:43]=[CH:42][C:41]([CH2:44]Cl)=[CH:40][CH:39]=2)=[CH:32][CH:31]=1>C(O)C.O>[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][O:37][C:38]2[CH:43]=[CH:42][C:41]([CH2:44][N:22]3[C:23](=[O:25])[N:24]=[C:19]([N:16]4[CH2:17][CH2:18][N:13]([C:10]5[CH:11]=[CH:12][C:7]([F:6])=[CH:8][CH:9]=5)[CH2:14][CH2:15]4)[NH:20][C:21]3=[O:26])=[CH:40][CH:39]=2)=[CH:32][CH:31]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
In argon atmosphere, to an N,N-dimethylformamide solution (5 mL) of 6-[4-(4-fluorophenyl)piperazin-1-yl]-1,3,5-triazine-2,4(1H,3H)-dione (200 mg, 0.69 mmol) synthesized in Reference Synthesis Example 18, lithium hydride (12 mg, 1.51 mmol) was added at 0° C. and the resultant mixture was stirred for 1 hour. To the mixture, 1-chloro-4-{[4-(chloromethyl)phenoxy]methyl}benzene (183 mg, 0.69 mmol) was added and the resultant mixture was stirred at 50° C. for 2 hours and at 70° C. for 3 days. After the completion of the reaction, water and ethanol were added to the reaction solution and a resultant solid was filtered to obtain a crude product of a precursor (66St) of the title compound, which was used as it was in the next reaction below.
Workup
- additionwas added at 0° C.
- additionwere added to the reaction solution
- filtrationa resultant solid was filtered
Sources & evidence
- ORD record
- ord-2089749750664417bf65e7ef4872c04a
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09403798B2
Reaction notes
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