N-Methylcyclohexylamine → Methyl 4-[4-(N-cyclohexyl-N-methyl-carbamoyl)-5-propylsulfanyl-pyrazol-1-yl]benzoate

HRID 1160519

반응식

HRID 1160519 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]([S:16][CH2:17][CH2:18][CH3:19])=[C:14]([C:20]([OH:22])=O)[CH:13]=[N:12]2)=[CH:7][CH:6]=1)=[O:4].[CH3:23][NH:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C>CN(C=O)C.C(OCC)(=O)C>[CH:25]1([N:24]([CH3:23])[C:20]([C:14]2[CH:13]=[N:12][N:11]([C:8]3[CH:7]=[CH:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:10][CH:9]=3)[C:15]=2[S:16][CH2:17][CH2:18][CH3:19])=[O:22])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

참가 물질

8

반응물 5

HCID 7514N-MethylcyclohexylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 595161221-(4-Methoxycarbonylphenyl)-5-propylsulfanyl-pyrazole-4-carboxylic acid2회

생성물 1

HCID 59516065Methyl 4-[4-(N-cyclohexyl-N-methyl-carbamoyl)-5-propylsulfanyl-pyrazol-1-yl]benzoate수율 78%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

1-(4-methoxycarbonylphenyl)-5-propylsulfanyl-pyrazole-4-carboxylic acid (Intermediate #7), (160 mg, 0.5 mmol), N-methylcyclohexylamine (57 mg, 0.5 mmol), HOBT (81 mg, 0.6 mmol) and DIPEA (174 μL, 1.0 mmol) were dissolved in DMF (5 mL) and treated at ambient temperature with EDCI (115 mg, 0.6 mmol). The mixture was stirred at ambient for 18 h and then diluted with ethyl acetate (50 mL), washed with water (3×20 mL) and brine, dried (MgSO4) and volatiles removed by evaporation. The residue was purified by chromatography on silica gel (12 g silica 0-70% EtOAc/isohexane) to give the title compound as a colourless gum (162 mg, 78%).

후처리

  1. washwashed with water (3×20 mL) and brine
  2. dry with materialdried (MgSO4) and volatiles
  3. customremoved by evaporation
  4. customThe residue was purified by chromatography on silica gel (12 g silica 0-70% EtOAc/isohexane)

출처 및 근거

ORD 기록
ord-51710cf94571423e8b5f510f34f473d9
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07816391B2

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