Cyclohexylamine → HCID 58961386, compound

HRID 1782059Notes

Reaction equation

HRID 1782059 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Al](C)(C)C.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[C:23]([CH2:24][N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)=[C:22]([C:30](OCC)=[O:31])[N:21]=[C:20]2[C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][C:36]=2[Cl:42])=[CH:15][CH:14]=1.C([O-])(O)=O.[Na+]>ClCCl.CCCCCCC>[CH:1]1([NH:7][C:30]([C:22]2[N:21]=[C:20]([C:35]3[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][C:36]=3[Cl:42])[N:19]([C:16]3[CH:15]=[CH:14][C:13]([Cl:12])=[CH:18][CH:17]=3)[C:23]=2[CH2:24][N:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[O:31])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 7965CyclohexylamineHCID 516892Sodium BicarbonateHCID 16682925TrimethylaluminumHCID 66885880HCID 66885880, compound

Product 1

HCID 58961386HCID 58961386, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8900HeptaneSolvent

Procedure

Part C: Cyclohexylamine (0.91 ml, 8 mmol) is dissolved in dichloromethane (20 ml) and (CH3)3Al (4 ml of a 2 M solution in heptane, 8 mmol) is added. The resulting mixture is stirred for 10 minutes at room temperature and ethyl 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-(pyrrolidin-1-ylmethyl)-1H-imidazole-4-carboxylate (1.8 gram, 3.8 mmol) is added. The resulting mixture is stirred at room temperature for 16 hours, poured into an aqueous NaHCO3 solution, stirred for 30 minutes and filtered over hyflo. The filtrated is twice extracted with dichloromethane. The organic layers are dried over Na2SO4, filtered and concentrated in vacuo. Subsequent purification with flash chromatography (dichloromethanelmethanol=98/2 (v/v)) gives N-cyclohexyl-1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-(pyrrolidin-1-ylmethyl)-1H-imidazole-4-carboxamide, compound 1 (1.06 gram, 53% yield). Melting point: 155-157° C.

Workup

  1. stirringThe resulting mixture is stirred at room temperature for 16 hours
  2. stirringstirred for 30 minutes
  3. filtrationfiltered over hyflo
  4. extractionThe filtrated is twice extracted with dichloromethane
  5. dry with materialThe organic layers are dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customSubsequent purification with flash chromatography (dichloromethanelmethanol=98/2 (v/v))

Sources & evidence

ORD record
ord-927809a31c014c9ab1479cdf5252b408
Source dataset
uspto-grants-2009_03
Patent number
US07498348B2

Reaction notes

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