Triethylamine → 5-Amino-2-(2-furyl)-7-(4-(imidazo[1,2-a]pyridin-2-ylmethyl)piperazinyl)[1,2,4]triazolo[1,5-c]pyrimidine

HRID 1264875Notes

Reaction equation

HRID 1264875 reaction equation
[NH2:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[O:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[C:6]2[CH:5]=[C:4]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[N:3]=1.[N:22]1[C:23]([CH2:31]Cl)=[CH:24][N:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=12.C(N(CC)CC)C.[OH-].[Na+]>CN(C=O)C.O>[NH2:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[O:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[C:6]2[CH:5]=[C:4]([N:16]2[CH2:17][CH2:18][N:19]([CH2:31][C:23]3[N:22]=[C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][N:25]4[CH:24]=3)[CH2:20][CH2:21]2)[N:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 9576142-Chloromethyl-imidazo(1,2-A)pyridineHCID 186136985-Amino-2-(2-furyl)-7-piperazinyl[1,2,4]triazolo[1,5-c]pyrimidine

Product 1

HCID 99316595-Amino-2-(2-furyl)-7-(4-(imidazo[1,2-a]pyridin-2-ylmethyl)piperazinyl)[1,2,4]triazolo[1,5-c]pyrimidineYield 51.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

In 7.5 mL of DMF, 500 mg (1.75 mmol) of Compound F and 582 mg (3.51 mmol) of imidazo[1,2-a]pyridin-2-ylmethyl chloride were dissolved. The solution was cooled to 0° C. in an ice bath, and then 1.6 mL of triethylamine was added thereto, followed by stirring at room temperature overnight. After completion of the reaction, water was added to the reaction mixture and a 1.0 mol/L sodium hydroxide solution was further added thereto to adjust the solution to be basic. Then, the mixture was extracted by adding chloroform, and the organic layer was washed with water and brine, and then dried over anhydrous magnesium sulfate. After evaporation of the solvent, the resulting residue was purified by silica gel column chromatography (2% methanol-chloroform) and then recrystallized from ethanol to obtain 374 mg of Compound 15 as white powder (yield: 51%).

Workup

  1. additionwas added to the reaction mixture
  2. extractionThen, the mixture was extracted
  3. additionby adding chloroform
  4. washthe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter evaporation of the solvent
  7. customthe resulting residue was purified by silica gel column chromatography (2% methanol-chloroform)
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-e64d6b3be6614073b4e2df73ee23e07c
Source dataset
uspto-grants-2003_04
Patent number
US06545000B1

Reaction notes

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