Oxalyl chloride → HCID 57749231, compound

HRID 1874418Notes

Reaction equation

HRID 1874418 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([OH:9])=O.C(Cl)(=O)C(Cl)=O.[NH2:16][C:17]1[CH:18]=[C:19]([CH:36]=[CH:37][CH:38]=1)[O:20][C:21]1[CH:22]=[CH:23][C:24]2[N:25]([N:27]=[C:28]([NH:30][C:31]([CH:33]3[CH2:35][CH2:34]3)=[O:32])[N:29]=2)[CH:26]=1>O1CCCC1.CN(C)C=O.O>[CH:33]1([C:31]([NH:30][C:28]2[N:29]=[C:24]3[CH:23]=[CH:22][C:21]([O:20][C:19]4[CH:18]=[C:17]([NH:16][C:7]([C:3]5[N:2]([CH3:1])[CH:6]=[CH:5][CH:4]=5)=[O:9])[CH:38]=[CH:37][CH:36]=4)=[CH:26][N:25]3[N:27]=2)=[O:32])[CH2:34][CH2:35]1

Participants

7

Reactant 3

HCID 65578Oxalyl chlorideHCID 814531-Methyl-2-pyrrolecarboxylic acidHCID 57749117N-[6-(3-aminophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide

Product 1

HCID 57749231HCID 57749231, compoundYield 41.6%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-methyl-1H-pyrrole-2-carboxylic acid (121 mg, 0.970 mmol) in tetrahydrofuran (5 mL) were added oxalyl chloride (169 μL, 1.94 mmol) and N,N-dimethylformamide (1 drop), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in N,N-dimethylacetamide (3 mL). N-[6-(3-Aminophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide (100 mg, 0.323 mmol) was added thereto with stirring under ice-cooling, and the mixture was stirred at room temperature for 15 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography (NH silica gel, ethyl acetate) and recrystallized from ethyl acetate to give the title compound (56.0 mg, 14%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in N,N-dimethylacetamide (3 mL)
  3. stirringwith stirring under ice-
  4. temperaturecooling
  5. stirringthe mixture was stirred at room temperature for 15 hr
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with water and saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltrated
  10. concentrationThe filtrate was concentrated under reduced pressure
  11. customthe residue was purified by column chromatography (NH silica gel, ethyl acetate)
  12. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c2100091cef247b499e46ef64c72974d
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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