Triethylamine → HCID 67259871, compound

HRID 79260Notes

Reaction equation

HRID 79260 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][N:9]2[C:12]([C:15]([OH:17])=O)=[CH:13][N:14]=[C:8]2[CH:7]=1.C(Cl)(=O)C(Cl)=O.[CH2:24]([N:31]1[C:39]2[CH:38]=[CH:37][CH:36]=[C:35]([NH2:40])[C:34]=2[C:33]([CH2:41][CH3:42])=[N:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(CC)CC)C>ClCCl.CN(C)C=O>[CH2:24]([N:31]1[C:39]2[C:34](=[C:35]([NH:40][C:15]([C:12]3[N:9]4[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:7][C:8]4=[N:14][CH:13]=3)=[O:17])[CH:36]=[CH:37][CH:38]=2)[C:33]([CH2:41][CH3:42])=[N:32]1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 667820257-(2-Methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxylic acidHCID 67259831HCID 67259831, compound

Product 1

HCID 67259871HCID 67259871, compoundYield 18.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

To a magnetically stirred suspension of 7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxylic acid (32.1 mg, 0.136 mmol) (prepared as in Example 1, steps A-D) in dry dichloromethane (1.5 mL), in a sealed vial, was added dry N,N-dimethylformamide (5 μL). The stirred mixture was cooled to 5° C. using ice bath. A solution of oxalyl chloride (86.8 μL, 0.174 mmol; 2M in dichloromethane) was added and the mixture was stirred for 10 minutes, occasionally allowing the resulting gases to vent. To the resulting solution was added 1-benzyl-3-ethyl-1H-indazol-4-amine (40 mg, 0.159 mmol) and triethylamine (30.2 μL, 0.217 mmol). The mixture was allowed to warm to ambient temperature and stirred for 16 hours. The mixture was evaporated to dryness under a stream of nitrogen. The resulting residue was purified using preparative thin layer chromatography, eluting with 5% methanol in dichloromethane. The material was further purified with a second preparative thin layer chromatography, eluting with 8% methanol in chloroform containing 0.5% ammonium hydroxide solution to provide N-(1-benzyl-3-ethyl-1H-indazol-4-yl)-7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxamide (12 mg). MS (APCI), positive scan, m/z=470.3 (M+H).

Workup

  1. temperatureto warm to ambient temperature
  2. stirringstirred for 16 hours
  3. customThe mixture was evaporated to dryness under a stream of nitrogen
  4. customThe resulting residue was purified
  5. washeluting with 5% methanol in dichloromethane
  6. customThe material was further purified with a second preparative thin layer chromatography
  7. washeluting with 8% methanol in chloroform containing 0.5% ammonium hydroxide solution

Sources & evidence

ORD record
ord-a056f62b746144f7a696c80f0d457024
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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