Water → N-(2-Chloro-4-methylpyridin-3-yl)-2-(cyclopropylamino)nicotinamide

HRID 1510811

Reaktionsgleichung

Reaktionsgleichung von HRID 1510811
Cl[C:2]1[C:7]([C:8]([NH:10][C:11]2[C:12]([Cl:18])=[N:13][CH:14]=[CH:15][C:16]=2[CH3:17])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[F-].[K+].[CH:21]1([NH2:24])[CH2:23][CH2:22]1.O>CC1C=CC=CC=1C>[Cl:18][C:12]1[C:11]([NH:10][C:8]([C:7]2[C:2]([NH:24][CH:21]3[CH2:23][CH2:22]3)=[N:3][CH:4]=[CH:5][CH:6]=2)=[O:9])=[C:16]([CH3:17])[CH:15]=[CH:14][N:13]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 69828CyclopropylamineHCID 522689Potassium FluorideHCID 104238682-Chloro-N-(2-chloro-4-methyl-3-pyridinyl)-3-pyridinecarboxamide

Produkt 1

HCID 9972204N-(2-Chloro-4-methylpyridin-3-yl)-2-(cyclopropylamino)nicotinamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel2×

Reaktionsbedingungen

Temperatur
135 °C

Versuchsvorschrift

2-Chloro-N-(2-chloro-4-methyl-3-pyridinyl)-3-pyridine carboxamide (100 g), potassium fluoride (22.62 g), cyclopropylamine (80.85 g) were suspended in o-xylene (300 ml) and heated to 130-140° C. in autoclave for 5-9 h. Then the reaction mass was cooled to 25-30° C., diluted with o-xylene (500 ml) and further heated the reaction mass to 70-75° C. Thereafter, DM water (300 ml) added and stirred for 10 min at 70-75° C. The aqueous layer was separated at hot condition and organic layer was washed with DM water (300 ml) at 70-75° C. and organic layer was concentrated at 60-63° C. under reduced pressure up to residue weight attained is approximately 400 g. The concentrated mass was cooled to 25-30° C. and stirred for 15 min and further cooled to 5-10° C. and stirred for 30 min. Filtered the solid obtained and washed with chilled o-xylene (100 ml, 5-10° C.). Dried the obtained solid at 50-60° C. under reduced pressure.

Aufarbeitung

  1. temperatureThen the reaction mass was cooled to 25-30° C.
  2. temperaturefurther heated the reaction mass to 70-75° C
  3. customThe aqueous layer was separated at hot condition and organic layer
  4. washwas washed with DM water (300 ml) at 70-75° C.
  5. concentrationorganic layer was concentrated at 60-63° C. under reduced pressure up to residue weight
  6. temperatureThe concentrated mass was cooled to 25-30° C.
  7. stirringstirred for 15 min
  8. temperaturefurther cooled to 5-10° C.
  9. stirringstirred for 30 min
  10. filtrationFiltered the solid
  11. customobtained
  12. washwashed with chilled o-xylene (100 ml, 5-10° C.)
  13. customDried the obtained solid at 50-60° C. under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f0479f02c46f43e5a248a3daa2e0b0d5
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08212025B2

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