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

HRID 79430ノート

反応式

HRID 79430 の反応式
CC(C)([O-])C.[K+].[CH3:7][N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][OH:16])[CH2:10][CH2:9]1.C(O)(C)(C)C.[CH:22]1([C:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][C:32]=3[NH:34][C:35]([C:37]3[N:41]4[CH:42]=[CH:43][C:44](F)=[CH:45][C:40]4=[N:39][CH:38]=3)=[O:36])[N:27]([CH2:47][C:48]3[C:49](=[O:55])[N:50]([CH3:54])[CH:51]=[CH:52][CH:53]=3)[N:26]=2)[CH2:24][CH2:23]1>O>[CH:22]1([C:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][C:32]=3[NH:34][C:35]([C:37]3[N:41]4[CH:42]=[CH:43][C:44]([O:16][CH2:15][CH2:14][N:11]5[CH2:12][CH2:13][N:8]([CH3:7])[CH2:9][CH2:10]5)=[CH:45][C:40]4=[N:39][CH:38]=3)=[O:36])[N:27]([CH2:47][C:48]3[C:49](=[O:55])[N:50]([CH3:54])[CH:51]=[CH:52][CH:53]=3)[N:26]=2)[CH2:24][CH2:23]1

参加物

6

反応物 4

HCID 6386tert-ButanolHCID 2311841-(2-Hydroxyethyl)-4-methylpiperazineHCID 23665647Potassium tert-butoxideHCID 67259522N-(3-cyclopropyl-1-((1-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1H-indazol-4-yl)-7-fluoroimidazo[1,2-a]pyridine-3-carboxamide

生成物 1

HCID 68333317N-(3-cyclopropyl-1-((1-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1H-indazol-4-yl)-7-(2-(4-methylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxamide

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A one dram vial was charged with solid potassium tert-butoxide (54 mg, 0.48 mmol), 2-(4-methylpiperazin-1-yl)ethanol (0.075 g, 0.52 mmol), and tert-butanol (0.3 mL, 3.4 mmol). The mixture was stirred at ambient temperature for 30 minutes. N-(3-cyclopropyl-1-((1-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1H-indazol-4-yl)-7-fluoroimidazo[1,2-a]pyridine-3-carboxamide (0.032 g, 0.070 mmol) was added in one portion. The mixture was heated at 88° C. with stirring for 16 hours. The mixture was cooled to ambient temperature and diluted with water until a precipitate formed. The precipitate was isolated by filtration and dried under high vacuum. Purification using silica preparative thin layer chromatography plate (20×20 cm, 0.5 mm) developed in a chamber with 10% methanol/dichloromethane with 0.6% concentrated ammonium hydroxide gave the product. MS (APCI), positive scan, m/z=581.2 (M+).

後処理

  1. temperatureThe mixture was heated at 88° C.
  2. stirringwith stirring for 16 hours
  3. temperatureThe mixture was cooled to ambient temperature
  4. customformed
  5. customThe precipitate was isolated by filtration
  6. customdried under high vacuum
  7. customPurification
  8. customgave the product

出典と根拠

ORDレコード
ord-02e9525120c848759abdcc7cc2833b34
出典データセット
uspto-grants-2014_09
特許番号
US08841455B2

反応ノート

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