Water → HCID 57749134, compound

HRID 1874612Notes

Reaction equation

HRID 1874612 reaction equation
[NH2:1][C:2]1[N:32]=[C:5]2[CH:6]=[CH:7][C:8]([O:10][C:11]3[CH:12]=[C:13]([NH:18][C:19](=[O:31])[C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([C:29]#[N:30])([CH3:28])[CH3:27])[CH:21]=4)[CH:14]=[CH:15][C:16]=3[CH3:17])=[CH:9][N:4]2[N:3]=1.C([O:36][CH2:37][C:38](Cl)=[O:39])(=O)C.C(=O)([O-])[O-].[K+].[K+].O>N1C=CC=CC=1>[C:29]([C:26]([C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][CH:23]=1)[C:19]([NH:18][C:13]1[CH:14]=[CH:15][C:16]([CH3:17])=[C:11]([O:10][C:8]2[CH:7]=[CH:6][C:5]3[N:4]([N:3]=[C:2]([NH:1][C:37](=[O:36])[CH2:38][OH:39])[N:32]=3)[CH:9]=2)[CH:12]=1)=[O:31])([CH3:28])[CH3:27])#[N:30]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 26297Acetoxyacetyl chlorideHCID 68985382N-{3-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]-4-methylphenyl}-3-(1-cyano-1-methylethyl)benzamide

Product 1

HCID 57749134HCID 57749134, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of N-{3-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]-4-methylphenyl}-3-(1-cyano-1-methylethyl)benzamide (203 mg, 0.477 mmol) in pyridine (10 mL) was added 2-chloro-2-oxoethyl acetate (103 μL, 0.954 mmol), and the mixture was stirred at room temperature for 17 hr. The reaction solution was concentrated under reduced pressure, and the residue was dissolved in methanol (10 mL). Potassium carbonate (132 mg, 0.954 mmol) was added thereto, and the mixture was stirred at room temperature for 1 hr. Water (30 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate (50 mL, 2×10 mL). The combined organic layer was washed with saturated brine (10 mL) and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. Ethyl acetate and diisopropyl ether were added to the obtained residue. The obtained precipitate was collected by filtration and dried to give the title compound (182 mg, 79%) as a colorless powder.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in methanol (10 mL)
  3. stirringthe mixture was stirred at room temperature for 1 hr
  4. extractionthe mixture was extracted with ethyl acetate (50 mL, 2×10 mL)
  5. washThe combined organic layer was washed with saturated brine (10 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe insoluble material was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. additionEthyl acetate and diisopropyl ether were added to the obtained residue
  10. filtrationThe obtained precipitate was collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-b457ffee49334685af23d3cbad9dc4a9
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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