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Hydrochloric Acid → 4-(cyclohexylmethyl)-5-{2-[4-(2-methoxyphenyl)piperazin-1-yl]propyl}-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 1514165
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HRID 1514165 반응식
[CH:1]1([CH2:7][NH:8][C:9]([NH:11][NH:12][C:13](=O)[CH2:14][CH:15]([N:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[O:29][CH3:30])[CH2:19][CH2:18]2)[CH3:16])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>[OH-].[Na+]>[CH:1]1([CH2:7][N:8]2[C:13]([CH2:14][CH:15]([N:17]3[CH2:22][CH2:21][N:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[O:29][CH3:30])[CH2:19][CH2:18]3)[CH3:16])=[N:12][NH:11][C:9]2=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1
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참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 59536457N-(cyclohexylmethyl)-2-{3-[4-(2-methoxyphenyl)piperazin-1-yl]butanoyl}hydrazinecarboxamide

생성물 1

HCID 251847324-(cyclohexylmethyl)-5-{2-[4-(2-methoxyphenyl)piperazin-1-yl]propyl}-2,4-dihydro-3H-1,2,4-triazol-3-one수율 48.8%

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매

실험 절차

N-(Cyclohexylmethyl)-2-{3-[4-(2-methoxyphenyl)piperazin-1-yl]butanoyl}hydrazinecarboxamide D13 (0.90 g, 2.08 mmol) in 2M NaOH aqueous solution (20 mL) was heated at reflux for 18 hrs. The pH was adjusted to 8 with conc. HCl and the resulting yellow slurry was extracted twice with DCM (50 mL and 20 mL). The combined organic extracts were filtered and DCM evaporated under reduced pressure to a light yellow glassy solid. Purification by flash chromatography (Silica gel 60 Å, 45 μm 10% methanol in dichloromethane) afforded 0.42 g (48.8%) 4-(cyclohexylmethyl)-5-{2-[4-(2-methoxyphenyl)piperazin-1-yl]propyl}-2,4-dihydro-3H-1,2,4-triazol-3-one D14 as a cream solid.

후처리

  1. temperatureat reflux for 18 hrs
  2. extractionthe resulting yellow slurry was extracted twice with DCM (50 mL and 20 mL)
  3. filtrationThe combined organic extracts were filtered
  4. customDCM evaporated under reduced pressure to a light yellow glassy solid
  5. customPurification by flash chromatography (Silica gel 60 Å, 45 μm 10% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-ef8ed5cbfb7941729cc8a028125b1892
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08222254B2

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