Sodium Bicarbonate → N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(2-oxoethyl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79447Notes

Reaction equation

HRID 79447 reaction equation
C([O:3]/[CH:4]=[CH:5]\[C:6]1[CH:11]=[CH:10][N:9]2[C:12]([C:15]([NH:17][C:18]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:19]=3[C:20]([CH2:35][CH3:36])=[N:21][N:22]4[CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[N:29]=3)=[O:16])=[CH:13][N:14]=[C:8]2[CH:7]=1)C.C(=O)(O)[O-].[Na+]>O1CCOCC1.O>[CH2:35]([C:20]1[C:19]2[C:23](=[CH:24][CH:25]=[CH:26][C:18]=2[NH:17][C:15]([C:12]2[N:9]3[CH:10]=[CH:11][C:6]([CH2:5][CH:4]=[O:3])=[CH:7][C:8]3=[N:14][CH:13]=2)=[O:16])[N:22]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[N:29]=2)[N:21]=1)[CH3:36]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 70814943(Z)-7-(2-ethoxyvinyl)-N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

Product 1

HCID 86672219N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(2-oxoethyl)imidazo[1,2-a]pyridine-3-carboxamideYield 95.6%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of (Z)-7-(2-ethoxyvinyl)-N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (211 mg, 0.439 mmol) in dioxane (6 mL) was treated at ambient temperature with 2.0 M HCl-ether. The resulting suspension was stirred at ambient temperature for 30 minutes. At that time 3 drops of water were added, so as not to collapse the suspension, and stirring was continued for another 30 minutes. The reaction mixture was neutralized with saturated aqueous sodium bicarbonate, extracted with DCM and EtOAc, and the combined organic extracts dried over anhydrous sodium sulfate. Concentration of the organic extracts afforded 190 mg of a solid which was used directly in next step.

Workup

  1. stirringstirring
  2. waitwas continued for another 30 minutes
  3. extractionextracted with DCM and EtOAc
  4. dry with materialthe combined organic extracts dried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-1cd4e0ef71814501a1f20d430a1d517a
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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