Chloroform → HCID 66778552, compound

HRID 406311Notes

Reaction equation

HRID 406311 reaction equation
O=[C:2]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:3][NH:4][C:5]([CH:7]1[CH2:12][CH2:11][CH2:10][N:9]2[N:13]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH:26]=[C:25]([CH3:27])[N:24]=[CH:23]4)=[C:18]([O:28][CH3:29])[N:17]=3)[N:15]=[C:8]12)=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:45])=CC=1.C(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>C1COCC1>[CH3:29][O:28][C:18]1[N:17]=[C:16]([C:14]2[N:15]=[C:8]3[CH:7]([C:5]4[S:45][C:2]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)=[CH:3][N:4]=4)[CH2:12][CH2:11][CH2:10][N:9]3[N:13]=2)[CH:21]=[CH:20][C:19]=1[N:22]1[CH:26]=[C:25]([CH3:27])[N:24]=[CH:23]1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 87949Lawesson's reagentHCID 516892Sodium BicarbonateHCID 66618765HCID 66618765, compound

Product 1

HCID 66778552HCID 66778552, compoundYield 10.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[6-Methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyridine-8-carboxylic acid (2-oxo-2-phenylethyl)amide obtained in Example 172 (26.6 mg) was dissolved in THF (1 mL). Lawesson reagent (45.6 mg) was added and the mixture was stirred with heating under reflux for 11 hours. The reaction solution was ice-cooled. Then, chloroform and a saturated sodium bicarbonate solution were added and the organic layer was separated. The resulting organic layer was dried over anhydrous sodium sulfate. The drying agent was separated by filtration and then the organic layer was concentrated under reduced pressure. The residue was purified by NH silica gel column chromatography to obtain the title compound (2.8 mg). The compound was further purified by CHIRALCEL™ IB (2 cm×25 cm; mobile phase:hexane:ethanol=30:70) to obtain the title compound (1.5 mg, racemate). The property values of the compound are as follows.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 11 hours
  3. temperaturecooled
  4. customthe organic layer was separated
  5. dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
  6. customThe drying agent was separated by filtration
  7. concentrationthe organic layer was concentrated under reduced pressure
  8. customThe residue was purified by NH silica gel column chromatography

Sources & evidence

ORD record
ord-d806062fe32144539adc6c2ed4a9c1c1
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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