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Cyclohexylamine → N-(1-cyclohexyl)-2-(2,4-dichlorophenyl)-5-methyl-1-(4-methoxyphenyl)-1H-imidazole-4-carboxamide

HRID 2215062
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HRID 2215062 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[C:11]([CH3:17])=[C:12]([C:14](O)=[O:15])[N:13]=1.C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[CH:59]1([NH2:65])[CH2:64][CH2:63][CH2:62][CH2:61][CH2:60]1>C(#N)C>[CH:59]1([NH:65][C:14]([C:12]2[N:13]=[C:9]([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])[N:10]([C:18]3[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=3)[C:11]=2[CH3:17])=[O:15])[CH2:64][CH2:63][CH2:62][CH2:61][CH2:60]1
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6

반응물 4

HCID 7965CyclohexylamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 111997572-(2,4-dichlorophenyl)-5-methyl-1-(4-methoxyphenyl)-1H-imidazole-4-carboxylic acid

생성물 1

HCID 10115332N-(1-cyclohexyl)-2-(2,4-dichlorophenyl)-5-methyl-1-(4-methoxyphenyl)-1H-imidazole-4-carboxamide
수율 85%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Part C: To 2-(2,4-dichlorophenyl)-5-methyl-1-(4-methoxyphenyl)-1H-imidazole-4-carboxylic acid (1.00 gram, 2.65 mmol) in dry acetonitrile (25 mL) is successively added diisopropylethylamine (DIPEA) (1.02 mL, 2.2 molar equivalents), O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluoro-phosphate (HBTU) (1.21 gram, 1.2 molar equivalents) and the resulting solution is stirred for 15 minutes. Cyclohexylamine (0.36 mL, 1.2 molar equivalents) is added. After stirring for 50 hours, the resulting mixture is concentrated in vacuo. The residue is dissolved in dichloromethane and an aqueous NaHCO3 solution is added. The dichloromethane layer is collected, dried over Na2SO4, filtered and concentrated in vacuo. The residue is further purified by column chromatography (gradient: dichloromethane=>dichloromethane/methanol=99/1 (v/v), silicagel) to give N-(1-cyclohexyl)-2-(2,4-dichlorophenyl)-5-methyl-1-(4-methoxyphenyl)-1H-imidazole-4-carboxamide (1.03 gram, 85% yield). Melting point: 160–161° C.

후처리

  1. stirringAfter stirring for 50 hours
  2. concentrationthe resulting mixture is concentrated in vacuo
  3. dissolutionThe residue is dissolved in dichloromethane
  4. additionan aqueous NaHCO3 solution is added
  5. customThe dichloromethane layer is collected
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue is further purified by column chromatography (gradient: dichloromethane=>dichloromethane/methanol=99/1 (v/v), silicagel)

출처 및 근거

ORD 기록
ord-f7f796dd550f4e3894318b74ec82a0ec
출처 데이터셋
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07109216B2

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