Morpholine → (1-Methyl-1H-pyrazol-4-yl)-morpholin-4-yl-methanone

HRID 1802313Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1802313
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]([OH:9])=O)[CH:4]=[N:3]1.C1C=CC2N(O)N=NC=2C=1.[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>C(Cl)Cl.O>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[O:9])[CH:4]=[N:3]1

Komponenten

6

Edukt 3

HCID 8083MorpholineHCID 757711-HydroxybenzotriazoleHCID 6431601-Methyl-1H-pyrazole-4-carboxylic acid

Produkt 1

HCID 39969381(1-Methyl-1H-pyrazol-4-yl)-morpholin-4-yl-methanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 1-methyl-1H-pyrazole-4-carboxylic acid (2.00 g, 15.9 mmol) in DCM (100 ml) and TEA (8.80 ml, 63.5 mmol), EDCHCl (3.65 g, 19.0 mmol) and HOBt (2.57 g, 19.0 mmol) were added under a nitrogen atmosphere at rt and stirred for 30 min. Morpholine (1.68 ml, 19.0 mmol) was then added to the reaction mixture and stirring was continued for 18 h. On completion of reaction (monitored by TLC), the reaction mixture was diluted with water and DCM. The organic layer was separated, dried over Na2SO4 and concentrated to get the crude product. Column chromatography afforded the desired product as off white solid. Yield: 1.20 g (39%); MS: m/z=196.4 ([M+H]+)

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for 18 h
  3. customOn completion of reaction (monitored by TLC)
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto get the crude product

Quellen und Nachweise

ORD-Eintrag
ord-fc99cbe5a9ce4a3dbd0dd6db330a4633
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349824B2

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