Citric Acid → N-(5-((2-(2,6-cis-Dimethylpiperidin-1-yl)ethyl)carbamoyl)-2-fluorophenyl)-7-(1-methyl-1H-pyrazol-5-yl)imidazo[1,2-a]pyridine-3-carboxamide Citric Acid

HRID 335277

Reaktionsgleichung

Reaktionsgleichung von HRID 335277
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([CH3:8])[N:3]1[CH2:9][CH2:10][NH:11][C:12]([C:14]1[CH:15]=[CH:16][C:17]([F:38])=[C:18]([NH:20][C:21]([C:23]2[N:27]3[CH:28]=[CH:29][C:30]([C:32]4[N:33]([CH3:37])[N:34]=[CH:35][CH:36]=4)=[CH:31][C:26]3=[N:25][CH:24]=2)=[O:22])[CH:19]=1)=[O:13].[C:39]([OH:51])(=[O:50])[CH2:40][C:41]([CH2:46][C:47]([OH:49])=[O:48])([C:43]([OH:45])=[O:44])[OH:42]>C(O)C.CC(C)=O>[C:39]([OH:51])(=[O:50])[CH2:40][C:41]([CH2:46][C:47]([OH:49])=[O:48])([C:43]([OH:45])=[O:44])[OH:42].[CH3:1][C@H:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([CH3:8])[N:3]1[CH2:9][CH2:10][NH:11][C:12]([C:14]1[CH:15]=[CH:16][C:17]([F:38])=[C:18]([NH:20][C:21]([C:23]2[N:27]3[CH:28]=[CH:29][C:30]([C:32]4[N:33]([CH3:37])[N:34]=[CH:35][CH:36]=4)=[CH:31][C:26]3=[N:25][CH:24]=2)=[O:22])[CH:19]=1)=[O:13]

Komponenten

5

Edukt 2

HCID 311Citric AcidHCID 780486287-(2-Methyl-2H-pyrazol-3-yl)-imidazo[1,2-a]pyridine-3-carboxylic Acid {5-[2-(2,6-dimethyl-piperidin-1-yl)-ethylcarbamoyl]-2-fluoro-phenyl}-amide

Produkt 1

HCID 71283110N-(5-((2-(2,6-cis-Dimethylpiperidin-1-yl)ethyl)carbamoyl)-2-fluorophenyl)-7-(1-methyl-1H-pyrazol-5-yl)imidazo[1,2-a]pyridine-3-carboxamide Citric Acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

7-(2-Methyl-2H-pyrazol-3-yl)-imidazo[1,2-a]pyridine-3-carboxylic acid {5-[2-(2,6-dimethyl-piperidin-1-yl)-ethylcarbamoyl]-2-fluoro-phenyl}-amide (step 3) (480 g) was suspended in ethanol (2300 mL) in a 5000 mL four-necked flask equipped with thermometer, reflux condenser and a nitrogen inlet. The mixture was heated to 55° C. and the suspension gradually became clear. A solution of citric acid (180 g) in acetone (2.4 L) was added over 1 h and the internal temperature was controlled at 45-50° C. The clear solution was stirred at 50° C. for 2 h. A crystal seed (1 g) was added to the reactor and the internal temperature was cooled to 20° C. at a speed of 8° C./h. The mixture was stirred at 20° C. for 60 h. The resulting solid was filtered and the filter cake was washed with acetone (1 L) and dried in vacuum (under 4 mbar at 55° C.) for 24 h to afford the title compound;

Aufarbeitung

  1. customequipped with thermometer
  2. temperaturereflux condenser and a nitrogen inlet
  3. customwas controlled at 45-50° C
  4. additionA crystal seed (1 g) was added to the reactor
  5. temperaturethe internal temperature was cooled to 20° C. at a speed of 8° C./h
  6. stirringThe mixture was stirred at 20° C. for 60 h
  7. filtrationThe resulting solid was filtered
  8. washthe filter cake was washed with acetone (1 L)
  9. customdried in vacuum (under 4 mbar at 55° C.) for 24 h

Quellen und Nachweise

ORD-Eintrag
ord-13124cc4631344a5b3c56b6b9401b446
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883819B2

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