Ethyl Acetate → HCID 24968473, compound

HRID 2369211Notes

Reaction equation

HRID 2369211 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6](SC)[C:5]([C:12]#[N:13])=[C:4]([S:14][CH2:15][C:16]2[N:17]=[C:18]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)[S:19][CH:20]=2)[N:3]=1.[OH:28][CH:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.[Cl-].[NH4+].C(OCC)(=O)C>CC(C)=O>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([N:32]2[CH2:33][CH2:34][CH:29]([OH:28])[CH2:30][CH2:31]2)[C:5]([C:12]#[N:13])=[C:4]([S:14][CH2:15][C:16]2[N:17]=[C:18]([C:21]3[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=3)[S:19][CH:20]=2)[N:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 79341Piperidin-4-olHCID 666721182-Amino-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}thio)-4-(methylthio)pyridine-3,5-dicarbonitrile

Product 1

HCID 24968473HCID 24968473, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

100 mg (0.23 mmol) of 2-amino-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}thio)-4-(methyl-thio)pyridine-3,5-dicarbonitrile and 1000 mg (9.89 mmol) of 4-hydroxypiperidine are combined in 2 ml of acetone and stirred under reflux for 8 h. The mixture is then added to a mixture of semiconcentrated aqueous ammonium chloride solution and ethyl acetate. After vigorous mixing, the organic phase is separated off, washed with saturated sodium chloride solution, dried over magnesium sulfate and filtered off using a glass frit, and the solvent is removed on a rotary evaporator. The residue is purified initially by column chromatography on silica gel 60 (mobile phase: gradient toluene/ethyl acetate 3:1→1:1) and then by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5). The title compound in obtained as a white powder.

Workup

  1. temperatureunder reflux for 8 h
  2. customAfter vigorous mixing, the organic phase is separated off
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered off
  6. customthe solvent is removed on a rotary evaporator
  7. customThe residue is purified initially by column chromatography on silica gel 60 (mobile phase: gradient toluene/ethyl acetate 3:1→1:1)

Sources & evidence

ORD record
ord-a494d58728904a19b14bf90e4c7afe2d
Source dataset
uspto-grants-2014_04
Patent number
US08703934B2

Reaction notes

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