Water → HCID 57928722, compound

HRID 1360188Notes

Reaction equation

HRID 1360188 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]=C)=[C:6]([NH:10][CH3:11])[N:5]=[CH:4][C:3]=1[C:12]([NH:14][NH:15][C:16](=O)[C:17]([O:19][CH3:20])=[O:18])=O.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:23].O.[OH-].[Na+]>O1CCCC1.O1CCOCC1>[CH3:20][O:19][C:17]([C:16]1[S:23][C:12]([C:3]2[C:2]([Cl:1])=[C:7]3[CH:8]=[CH:11][NH:10][C:6]3=[N:5][CH:4]=2)=[N:14][N:15]=1)=[O:18]

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 14817Phosphorus sulfide (P2S5)2×HCID 66924284HCID 66924284, compound

Product 1

HCID 57928722HCID 57928722, compoundYield 35.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of methyl (2-{[4-chloro-6-(methylamino)-5-vinylpyridine-3-yl]carbonyl}hydrazino)(oxo)acetate (450 mg) in tetrahydrofuran (7 ml) and dioxane (7 ml) was added diphosphorus pentasulfide (383 mg) under cooling in an ice bath. After the mixture was stirred at ambient temperature for 5 hours. To the reaction mixture was added tetrahydrofuran (10 ml) and diphosphorus pentasulfide (190 mg). After the mixture was stirred at ambient temperature for 2 hours, water was added to the reaction solution, and the pH was adjusted to approximately 10 with aqueous sodium hydroxide, and the solution was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (chloroform:methanol) to obtain methyl-5-(4-chloro-1H-pyrrolo[2,3,b]pyridine-5-yl)-1,3,4-thiadiazole-2-carboxylate (90 mg).

Workup

  1. temperatureunder cooling in an ice bath
  2. stirringAfter the mixture was stirred at ambient temperature for 2 hours
  3. extractionthe solution was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (chloroform:methanol)

Sources & evidence

ORD record
ord-d6066641ec2d4918a1183fe5ab7568de
Source dataset
uspto-grants-2011_02
Patent number
US07879844B2

Reaction notes

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