Trisodium phosphate dodecahydrate → N-(2-Chloro-4-methylpyridin-3-yl)-2-(cyclopropylamino)nicotinamide

HRID 1510813

Reaktionsgleichung

Reaktionsgleichung von HRID 1510813
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.O.O.O.O.O.O.O.O.O.O.O.O.P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+].[CH:39]1([NH2:42])[CH2:41][CH2:40]1>CC1C=CC=CC=1C.O>[Cl:18][C:12]1[C:11]([NH:10][C:8]([C:7]2[C:2]([NH:42][CH:39]3[CH2:41][CH2:40]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 3

HCID 61473Trisodium phosphate dodecahydrateHCID 69828CyclopropylamineHCID 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 2

HCID 962WaterLösungsmittelHCID 7237O-XyleneLösungsmittel2×

Reaktionsbedingungen

Temperatur
135 °C

Versuchsvorschrift

2-Chloro-N-(2-chloro-4-methyl-3-pyridinyl)-3-pyridine carboxamide (15 g), trisodium phosphate dodecahydrate (20.21 g), cyclopropylamine (12.12 g) were suspended in o-xylene (45 ml) and heated to 130-140° C. for 6-8 h in S.S. Bomb with occasional shaking. Then the reaction mass was cooled to 70-75° C., diluted with o-xylene (75 ml) and DM water (45 ml) and stirred for 10 min at 70-80° C. The aqueous layer was separated and washed the organic layer with DM water (45 ml) at 70-80° C. The organic layer was concentrated at 60-65° C. under reduced pressure. The concentrated mass was cooled to 5-10° C. and stirred for 30 min. Filtered the solid obtained and washed with chilled o-xylene (15 ml, 5-10° C.). Dried the obtained solid at 55-60° C. under reduced pressure.

Aufarbeitung

  1. temperatureThen the reaction mass was cooled to 70-75° C.
  2. customThe aqueous layer was separated
  3. washwashed the organic layer with DM water (45 ml) at 70-80° C
  4. concentrationThe organic layer was concentrated at 60-65° C. under reduced pressure
  5. temperatureThe concentrated mass was cooled to 5-10° C.
  6. stirringstirred for 30 min
  7. filtrationFiltered the solid
  8. customobtained
  9. washwashed with chilled o-xylene (15 ml, 5-10° C.)
  10. customDried the obtained solid at 55-60° C. under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-04b544f771af4d07817925556a9a0f07
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08212025B2

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