Chloroform → HCID 66670343, compound

HRID 1514655Notes

Reaction equation

HRID 1514655 reaction equation
[NH2:1][C:2](=[N:4][C:5]([C:7]1[CH:8]=[C:9]([CH:22]2[CH2:27][CH2:26][N:25](C(OCC3C=CC=CC=3)=O)[CH2:24][CH2:23]2)[N:10]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[C:11]=1[CH3:12])=[O:6])[NH2:3].C(Cl)(Cl)[Cl:39]>C(O)C.[Pd]>[ClH:39].[ClH:39].[NH2:3][C:2]([NH2:1])=[N:4][C:5]([C:7]1[CH:8]=[C:9]([CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[N:10]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[C:11]=1[CH3:12])=[O:6]

Participants

5

Reactant 2

HCID 6212ChloroformHCID 66670381HCID 66670381, compound

Product 1

HCID 66670343HCID 66670343, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A 230 mg portion of benzyl 4-{4-{[(diaminomethylene)amino]carbonyl}-1-[2-(4-fluorophenyl)ethyl]-5-methyl-1H-pyrrol-2-yl}piperidine-1-carboxylate was dissolved in 5 ml of ethanol, 45 mg of 10% palladium-activated carbon was added, followed by stirring at room temperature for 5 hours under an atmosphere of hydrogen. After adding chloroform to the reaction liquid, the insoluble matter was separated by celite filtration, and the filtrate was concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (Chromatorex (registered trademark), methanol:chloroform=10:90). The resulting product was dissolved in 3 ml of ethanol, and 0.269 ml of 4 M hydrogen chloride/ethyl acetate was added under ice-cooling, followed by stirring overnight at room temperature. The resulting solid was collected by filtration to obtain 95 mg of N-(diaminomethylene)-1-[2-(4-fluorophenyl)ethyl]-2-methyl-5-piperidin-4-yl-1H-pyrrole-3-carboxamide dihydrochloride as a white solid.

Workup

  1. customto the reaction liquid
  2. customthe insoluble matter was separated by celite filtration
  3. concentrationthe filtrate was concentrated under a reduced pressure
  4. customThe residue was purified by silica gel column chromatography (Chromatorex (registered trademark), methanol:chloroform=10:90)
  5. dissolutionThe resulting product was dissolved in 3 ml of ethanol
  6. addition0.269 ml of 4 M hydrogen chloride/ethyl acetate was added under ice-
  7. temperaturecooling
  8. stirringby stirring overnight at room temperature
  9. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-e3d78ccc44d446069f2a4b5f6673f7e8
Source dataset
uspto-grants-2012_07
Patent number
US08222274B2

Reaction notes

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