3-Pyridineacetic acid → N-[2-(5-Methyl-3-phenyl-isoxazol-4-yl)-imidazo[1,2-a]pyridin-7-yl]-2-pyridin-3-yl-acetamide

HRID 731644

Reaction equation

HRID 731644 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[N:14]=[C:15]2[CH:20]=[C:19]([NH2:21])[CH:18]=[CH:17][N:16]2[CH:22]=1.[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][C:30](O)=[O:31])[CH:24]=1.C(N(CC)C(C)C)(C)C.[Cl-].[Na+].O.O>CN(C=O)C>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:3]=1[C:13]1[N:14]=[C:15]2[CH:20]=[C:19]([NH:21][C:30](=[O:31])[CH2:29][C:25]3[CH:24]=[N:23][CH:28]=[CH:27][CH:26]=3)[CH:18]=[CH:17][N:16]2[CH:22]=1

Participants

6

Reactant 4

HCID 1083-Pyridineacetic acidHCID 81531DiisopropylethylamineHCID 23713072Sodium chloride dihydrateHCID 247388302-(5-Methyl-3-phenyl-isoxazol-4-yl)-imidazo[1,2-a]pyridin-7-ylamine

Product 1

HCID 69067454N-[2-(5-Methyl-3-phenyl-isoxazol-4-yl)-imidazo[1,2-a]pyridin-7-yl]-2-pyridin-3-yl-acetamideYield 4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2-(5-methyl-3-phenyl-isoxazol-4-yl)-imidazo[1,2-a]pyridin-7-ylamine (92 mg, 0.32 mmol) in DMF (0.2 mL) was added to a solution containing 3-pyridylacetic acid (39.5 mg, 0.29 mmol), N,N,N′,N′-tetramethyl-O-(benzotriazol-1-yl)uranium tetrafluoroborate (101.7 mg, 0.32 mmol), N,N-diisopropyl ethyl amine (247 μL, 1.44 mmol) in DMF (0.3 mL) and the resulting mixture stirred at room temperature overnight and then heated at 110° C. for 6 h. The resulting mixture was then poured into a mixture of brine: water (1:1) and extracted with ethyl acetate. The combined organic layers were then washed with brine, dried over sodium sulphate and evaporated to leave a brown solid. Purification by chromatography (SiO2, dichloromethane:methanol=90:10) afforded the title compound (4.3 mg, 4%) which was obtained as a yellow oil. MS: m/e=410.1 [M+H]+.

Workup

  1. temperatureheated at 110° C. for 6 h
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were then washed with brine
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customto leave a brown solid
  7. customPurification by chromatography (SiO2, dichloromethane:methanol=90:10)

Sources & evidence

ORD record
ord-4e920a2b62724b05aba1cd0437c7c4a9
Source dataset
uspto-grants-2009_09
Patent number
US07585874B2

Linked notes

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