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

HRID 2215062
Notes
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Reaction equation

HRID 2215062 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-f7f796dd550f4e3894318b74ec82a0ec
Source dataset
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07109216B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes