Nicotinoyl chloride → N-{6-[5-({[3-(1-cyano-1-methylethyl)phenyl]carbonyl}amino)-2-methylphenoxy][1,2,4]triazolo[1,5-a]pyridin-2-yl}pyridine-3-carboxamide

HRID 1874608Notes

Reaction equation

HRID 1874608 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.[N:33]1[CH:38]=[CH:37][CH:36]=[C:35]([C:39](Cl)=[O:40])[CH:34]=1.C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[C:29]([C:26]([C:22]1[CH:21]=[C:20]([C:19]([NH:18][C:13]2[CH:14]=[CH:15][C:16]([CH3:17])=[C:11]([CH:12]=2)[O:10][C:8]2[CH:7]=[CH:6][C:5]3[N:4]([N:3]=[C:2]([NH:1][C:39]([C:35]4[CH:34]=[N:33][CH:38]=[CH:37][CH:36]=4)=[O:40])[N:32]=3)[CH:9]=2)=[O:31])[CH:25]=[CH:24][CH:23]=1)([CH3:28])[CH3:27])#[N:30]

Participants

5

Reactant 3

HCID 82604Nicotinoyl chlorideHCID 516892Sodium BicarbonateHCID 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 57749230N-{6-[5-({[3-(1-cyano-1-methylethyl)phenyl]carbonyl}amino)-2-methylphenoxy][1,2,4]triazolo[1,5-a]pyridin-2-yl}pyridine-3-carboxamideYield 98.3%

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 (200 mg, 0.469 mmol) in pyridine (5 mL) was added pyridine-3-carbonyl hydrochloride (212 mg, 1.19 mmol), and the mixture was stirred at room temperature for 3 hr. A saturated aqueous sodium hydrogen carbonate solution (20 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate (20 mL, 5 mL). The combined organic layer was washed with saturated brine (5 mL) and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. Ethyl acetate was added to the obtained residue. The obtained precipitate was collected by filtration and dried to give the title compound (245 mg, 97%) as a colorless powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (20 mL, 5 mL)
  2. washThe combined organic layer was washed with saturated brine (5 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe insoluble material was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionEthyl acetate was added to the obtained residue
  7. filtrationThe obtained precipitate was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-0db776af83774541bca827844bc8ca6e
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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