Imidazole → 4-{[({[2-(Carbamoylmethyl)phenyl]amino}thioxomethyl)amino]methyl}piperidine carboxylic acid tert-butyl ester

HRID 2110044Notes

Reaction equation

HRID 2110044 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH2:15])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:16]([N:23]1[CH:27]=[CH:26]N=C1)(N1C=CN=C1)=[S:17].N1C=CN=C1.N[C:34]1[CH:39]=[CH:38]C=C[C:35]=1[CH2:40][C:41]([NH2:43])=[O:42]>C(#N)C>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]([NH:23][C:27]2[CH:26]=[CH:38][CH:39]=[CH:34][C:35]=2[CH2:40][C:41](=[O:42])[NH2:43])=[S:17])[CH2:10][CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 802641,1'-ThiocarbonyldiimidazoleHCID 2782862-(2-Aminophenyl)acetamideHCID 7368171-Boc-4-(aminomethyl)piperidine

Product 1

HCID 866105084-{[({[2-(Carbamoylmethyl)phenyl]amino}thioxomethyl)amino]methyl}piperidine carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

After dissolving 1-N-Boc-4-aminomethylpiperidine (869 mg, 4.06 mmol) in acetonitrile (10 mL), a solution of thiocarbonyldiimidazole (794 mg, 4.46 mmol) and imidazole (82.9 mg, 1.22 mmol) in acetonitrile (15 mL) was added dropwise in an ice bath, and the mixture was stirred at room temperature for 4 hours. After then adding 2-(2-aminophenyl)acetamide (670 mg, 4.46 mmol) thereto, the mixture was stirred overnight at 60° C. The reaction mixture was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (methylene chloride/methanol=65:1→49:1) to obtain the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe obtained residue was purified by silica gel column chromatography (methylene chloride/methanol=65:1→49:1)

Sources & evidence

ORD record
ord-221f31db34c942319a3cb7052eb6bed2
Source dataset
uspto-grants-2009_04
Patent number
US07517875B2

Reaction notes

Loading…