4-Methylmorpholine → 5-Tert-butyl-pyridine-2-carboxylic acid [2-(3,4-dichloro-phenyl)-ethyl]-amide

HRID 2243188

Reaktionsgleichung

Reaktionsgleichung von HRID 2243188
[OH-].[K+].CO[C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:9][N:8]=1)=[O:6].[Cl:17][C:18]1[CH:19]=[C:20]([CH2:25][CH2:26][NH2:27])[CH:21]=[CH:22][C:23]=1[Cl:24].CN1CCOCC1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C1COCC1>[Cl:17][C:18]1[CH:19]=[C:20]([CH2:25][CH2:26][NH:27][C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:9][N:8]=2)=[O:6])[CH:21]=[CH:22][C:23]=1[Cl:24]

Komponenten

7

Edukt 5

HCID 79724-MethylmorpholineHCID 14797Potassium HydroxideHCID 2179583,4-DichlorophenethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10774153Methyl 5-(tert-butyl)picolinate

Produkt 1

HCID 670177025-Tert-butyl-pyridine-2-carboxylic acid [2-(3,4-dichloro-phenyl)-ethyl]-amideAusbeute 58,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Potassium hydroxide (2 M aq. solution, 0.98 mL, 1.96 mmol) was added at RT to a solution of 5-tert-butyl-pyridine-2-carboxylic acid methyl ester (synthesized according to J. Org. Chem. 1998, 63, 7840-7850; 189 mg, 0.98 mmol) in THF (2.6 mL), then after stirring for 2 h, the reaction mixture was evaporated. The residue was taken up in DMF (12 mL), then after addition of 2-(3,4-dichloro-phenyl)-ethylamine (204 mg, 1.07 mmol), 4-methylmorpholine (297 mg, 2.93 mmol), and HBTU (556 mg, 1.47 mmol), the reaction mixture was stirred at RT for 16 h, then partitioned between water and ethyl acetate. The organic layer was washed with brine, dried (MgSO4), and concentrated. Chromatography (SiO2, heptane-ethyl acetate gradient) produced 5-tert-butyl-pyridine-2-carboxylic acid [2-(3,4-dichloro-phenyl)-ethyl]-amide (200 mg, 58%). White solid, MS (ISP): 351.4 (M+H)+.

Aufarbeitung

  1. customthe reaction mixture was evaporated
  2. stirringthe reaction mixture was stirred at RT for 16 h
  3. custompartitioned between water and ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-457ea0d6351e45cea2190369d974942f
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07674815B2

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