Hydrochloric Acid → 1-(4-chlorophenyl)-N-methyl-5-phenyl-N''-(piperidin-1-ylsulfonyl)-4,5-dihydro-1H-pyrazole-3-carboximidamide

HRID 19762ノート

反応式

HRID 19762 の反応式
[N:1]1([S:7]([NH:10][C:11]([C:13]2[CH2:17][CH:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:15]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[N:14]=2)=O)(=[O:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.P(Cl)(Cl)(Cl)(Cl)Cl.Cl.C[CH2:39][N:40](C(C)C)C(C)C>ClC1C=CC=CC=1>[N:1]1([S:7]([NH:10][C:11]([C:13]2[CH2:17][CH:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:15]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[N:14]=2)=[N:40][CH3:39])(=[O:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 24819Phosphorus pentachlorideHCID 81531DiisopropylethylamineHCID 68692403N-[(piperidin-1-yl)sulfonyl]-1-(4-chlorophenyl)-5-phenyl-4,5-dihydro-(1H)-pyrazole-3-carboxamide

生成物 1

HCID 117122961-(4-chlorophenyl)-N-methyl-5-phenyl-N''-(piperidin-1-ylsulfonyl)-4,5-dihydro-1H-pyrazole-3-carboximidamide収率 49%

試薬・触媒・溶媒 1

HCID 7964Chlorobenzene溶媒

反応条件

温度
140 °C

実験手順

Part B: A stirred mixture of N-[(piperidin-1-yl)sulfonyl]-1-(4-chlorophenyl)-5-phenyl-4,5-dihydro-(1H)-pyrazole-3-carboxamide (2.23 gram, 5 mmol), PCl5 (1.15 g, 5.5 mmol) and chlorobenzene (50 ml) is heated for 90 minutes at 140° C. After cooling the mixture to room temperature, followed by concentration in vacuo, the residue is dissolved in dichloromethane and methylamine.HCl (0.34 g, 5 mmol) and DIPEA (1.74 ml, 10 mmol) are successively added. The resulting mixture is stirred for 1 hour at room temperature, twice washed with water, dried over MgSO4, filtered and concentrated in vacuo. The resulting residue is further purified by flash chromatography (silica gel, dichloromethane), followed by crystallization from diisopropyl ether to give N-[(piperidin-1-yl)sulfonyl]-N′-methyl-1-(4-chlorophenyl)-5-phenyl-4,5-dihydro-(1H)-pyrazole-3-carboxamidine (1.12 gram, 49% yield). Melting point: 141-144° C. Rf (silica gel, diethyl ether=0.2).

後処理

  1. temperatureAfter cooling the mixture to room temperature
  2. concentrationfollowed by concentration in vacuo
  3. dissolutionthe residue is dissolved in dichloromethane
  4. stirringThe resulting mixture is stirred for 1 hour at room temperature
  5. washtwice washed with water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting residue is further purified by flash chromatography (silica gel, dichloromethane)
  10. customfollowed by crystallization from diisopropyl ether

出典と根拠

ORDレコード
ord-485028f1bd454ea9b7e27e459b6630d6
出典データセット
uspto-grants-2010_06
特許番号
US07745476B2

反応ノート

読み込み中…