Water → 4-chloro-2-(N-(2-morpholin-4-ylethyl)carbamoyl)pyridine

HRID 491072

Reaktionsgleichung

Reaktionsgleichung von HRID 491072
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]([O:11]C)=O)[CH:4]=1.[NH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.O>C1COCC1>[Cl:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9](=[O:11])[NH:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH:4]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 4082852-MorpholinoethylamineHCID 16655470Methyl 4-chloropyridine-2-carboxylate--hydrogen chloride (1/1)

Produkt 1

HCID 236145794-chloro-2-(N-(2-morpholin-4-ylethyl)carbamoyl)pyridineAusbeute 95,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of methyl 4-chloropyridine-2-carboxylate HCl salt (Method A2, Step 2; 1.01 g, 4.86 mmol) in THF (20 mL) was added 4-(2-aminoethyl)morpholine (2.55 mL, 19.4 mmol) dropwise and the resulting solution was heated at the reflux temp. for 20 h, cooled to room temp., and treated with water (50 mL). The resulting mixture was extracted with EtOAc (50 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure to afford 4-chloro-2-(N-(2-morpholin-4-ylethyl)carbamoyl)pyridine as a yellow oil (1.25 g, 95%): TLC (10% MeOH/90% EtOAc) Rf0.50.

Aufarbeitung

  1. temperaturethe resulting solution was heated at the reflux temp
  2. temperaturecooled to room temp.
  3. extractionThe resulting mixture was extracted with EtOAc (50 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6242253afe50426fb3d68246df44c185
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07528255B2

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