tert-Butanol → N-(3-cyclopropyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(2-(4-isopropylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79424Notes

Reaction equation

HRID 79424 reaction equation
CC(C)([O-])C.[K+].[CH:7]([N:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][OH:18])[CH2:12][CH2:11]1)([CH3:9])[CH3:8].C(O)(C)(C)C.F[C:25]1[CH:30]=[CH:29][N:28]2[C:31]([C:34]([NH:36][C:37]3[CH:45]=[CH:44][CH:43]=[C:42]4[C:38]=3[C:39]([CH:54]3[CH2:56][CH2:55]3)=[N:40][N:41]4[CH2:46][C:47]3[CH:52]=[CH:51][CH:50]=[C:49]([CH3:53])[N:48]=3)=[O:35])=[CH:32][N:33]=[C:27]2[CH:26]=1>O>[CH:54]1([C:39]2[C:38]3[C:42](=[CH:43][CH:44]=[CH:45][C:37]=3[NH:36][C:34]([C:31]3[N:28]4[CH:29]=[CH:30][C:25]([O:18][CH2:17][CH2:16][N:13]5[CH2:12][CH2:11][N:10]([CH:7]([CH3:9])[CH3:8])[CH2:15][CH2:14]5)=[CH:26][C:27]4=[N:33][CH:32]=3)=[O:35])[N:41]([CH2:46][C:47]3[CH:52]=[CH:51][CH:50]=[C:49]([CH3:53])[N:48]=3)[N:40]=2)[CH2:56][CH2:55]1

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 47396302-(4-Isopropylpiperazin-1-yl)ethanolHCID 23665647Potassium tert-butoxideHCID 672611757-Fluoro-N-(3-cyclopropyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

Product 1

HCID 67259619N-(3-cyclopropyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(2-(4-isopropylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxamideYield 41.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A one dram vial was charged with solid potassium tert-butoxide (55 mg, 0.49 mmol), 2-(4-isopropylpiperazin-1-yl)ethanol (0.099 g, 0.57 mmol), and tert-butanol (0.3 mL, 3.4 mmol). The mixture was stirred at ambient temperature for 30 minutes. 7-Fluoro-N-(3-cyclopropyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (0.034 g, 0.077 mmol) was added in one portion. The mixture was heated at 90° C. with stirring for 16 hours. The mixture was cooled to ambient temperature and diluted with water until a precipitate formed. The precipitate was collected by filtration and dried under high vacuum to give the product (0.019 g). MS (APCI), positive scan, m/z=593.1 (M+H).

Workup

  1. temperatureThe mixture was heated at 90° C.
  2. stirringwith stirring for 16 hours
  3. temperatureThe mixture was cooled to ambient temperature
  4. customformed
  5. filtrationThe precipitate was collected by filtration
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-4450c944e60c4bcf9100ac6af9cdb30c
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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