Dimethylformamide → 4-[4-(4-Fluorophenyl)piperazin-1-yl]-1-{[5-(trifluoromethyl)thiophen-2-yl]methyl}-1,3,5-triazin-2(1H)-one

HRID 1477692ノート

反応式

HRID 1477692 の反応式
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[N:24]=[CH:23][NH:22][C:21](=[O:25])[N:20]=3)[CH2:15][CH2:14]2)=[CH:9][CH:8]=1.CC1C=CC(S(O[CH2:37][C:38]2[S:39][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:41][CH:42]=2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O>[F:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:14][CH2:15][N:16]([C:19]3[N:24]=[CH:23][N:22]([CH2:37][C:38]4[S:39][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:41][CH:42]=4)[C:21](=[O:25])[N:20]=3)[CH2:17][CH2:18]2)=[CH:9][CH:8]=1

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 117839221[5-(Trifluoromethyl)thiophen-2-yl]methyl 4-methylbenzenesulfonate2 回HCID 178517893HCID 178517893、化合物

生成物 1

HCID 1179254934-[4-(4-Fluorophenyl)piperazin-1-yl]-1-{[5-(trifluoromethyl)thiophen-2-yl]methyl}-1,3,5-triazin-2(1H)-one収率 12%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To an N,N-dimethylformamide solution (1 mL) of 4-[4-(4-fluorophenyl)piperazin-1-yl]-1,3,5-triazin-2(1H)-one (50.0 mg, 0.18 mmol) synthesized in Reference Synthesis Example 3, [5-(trifluoromethyl)thiophen-2-yl]methyl 4-methylbenzenesulfonate (121 mg, 0.36 mmol) synthesized in Reference Synthesis Example 51 and potassium carbonate (99 mg, 0.72 mmol) were added and the resultant mixture was stirred at 80° C. for 2 hours. To the reaction solution, [5-(trifluoromethyl)thiophen-2-yl]methyl 4-methylbenzenesulfonate (500 mg, 0.48 mmol) was added and the resultant reaction solution was stirred further for 2 hours. After the completion of the reaction, water was added to the reaction solution and extraction with ethyl acetate from the resultant reaction solution was performed three times. The organic layer was washed with brine, was dried over anhydrous magnesium sulfate, and was concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1) to obtain the title compound (9.4 mg, yield: 12%).

後処理

  1. additionwere added
  2. customthe resultant reaction solution
  3. customreaction solution
  4. washThe organic layer was washed with brine
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. concentrationwas concentrated under reduced pressure
  7. customThe resultant residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)

出典と根拠

ORDレコード
ord-a5217f96a53b4da6993e62cf9f4aef6f
出典データセット
uspto-grants-2016_08
特許番号
US09403798B2

反応ノート

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