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

HRID 19762노트

반응식

HRID 19762 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 7964Chlorobenzene용매

반응 조건

온도
140 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-485028f1bd454ea9b7e27e459b6630d6
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745476B2

반응 노트

불러오는 중…