Cyclopentanone → 6-[(3-Cyclopentyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-N-methyl-3-pyridinecarboxamide

HRID 222723Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 222723
[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([O:11][C:12]2[CH:22]=[CH:21][C:15]3[CH2:16][CH2:17][NH:18][CH2:19][CH2:20][C:14]=3[CH:13]=2)=[CH:9][CH:10]=1)=[O:4].[C:23]1(=O)[CH2:27][CH2:26][CH2:25][CH2:24]1>C(O)(=O)C.CO>[CH:23]1([N:18]2[CH2:17][CH2:16][C:15]3[CH:21]=[CH:22][C:12]([O:11][C:8]4[N:7]=[CH:6][C:5]([C:3]([NH:2][CH3:1])=[O:4])=[CH:10][CH:9]=4)=[CH:13][C:14]=3[CH2:20][CH2:19]2)[CH2:27][CH2:26][CH2:25][CH2:24]1

Komponenten

5

Edukt 2

HCID 8452CyclopentanoneHCID 57440288N-Methyl-6-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yloxy)-3-pyridinecarboxamide

Produkt 1

HCID 104289246-[(3-Cyclopentyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-N-methyl-3-pyridinecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

N-Methyl-6-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yloxy)-3-pyridinecarboxamide (D40) (150 mg, 0.5 mmol) was dissolved in 2.5% acetic acid in methanol (5 ml) and treated dropwise with cyclopentanone (0.09 ml, 1 mmol). The mixture was stirred for 30 minutes and then (polystyrylmethyl)trimethylammonium cyanoborohydride (2.04 mmol/g, 490 mg, 0.1 mmol) was added. The reaction mixture was stirred at room temperature for 14 hours, applied to a SCX cartridge (Varian bond-elute, 10 g) and washed with methanol and then a mixture of 0.880 ammonia/methanol. The combined basic fractions were concentrated in vacuo and the resulting residue purified by column chromatography eluting with a mixture of 0.880 ammonia:methanol:dichloromethane (0.25:2.25:97.5) to afford the title compound (E223). MS (ES+) m/e 366 [M+H]+.

Aufarbeitung

  1. stirringThe reaction mixture was stirred at room temperature for 14 hours
  2. washwashed with methanol
  3. additiona mixture of 0.880 ammonia/methanol
  4. concentrationThe combined basic fractions were concentrated in vacuo
  5. customthe resulting residue purified by column chromatography
  6. washeluting with a mixture of 0.880 ammonia:methanol:dichloromethane (0.25:2.25:97.5)

Quellen und Nachweise

ORD-Eintrag
ord-5713405e45984f328d3eed8ff2134e79
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207331B2

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