Butyl iodide → 1-[6-Amino-5-chloro-2-(methoxy)-3-pyridinyl]-3-(1-butyl-4-piperidinyl)-1-propanone

HRID 489795Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 489795
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([C:10](=[O:19])[CH2:11][CH2:12][CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:4][C:3]=1[Cl:20].I[CH2:22][CH2:23][CH2:24][CH3:25].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(OCC)(=O)C>[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([C:10](=[O:19])[CH2:11][CH2:12][CH:13]2[CH2:18][CH2:17][N:16]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:15][CH2:14]2)=[CH:4][C:3]=1[Cl:20]

Komponenten

6

Edukt 3

HCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 222625871-(6-Amino-5-chloro-2-methoxy-3-pyridinyl)-3-(4-piperidinyl)-1-propanone

Produkt 1

HCID 222626001-[6-Amino-5-chloro-2-(methoxy)-3-pyridinyl]-3-(1-butyl-4-piperidinyl)-1-propanoneAusbeute 70,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 1-[6-amino-5-chloro-2-(methyloxy)-3-pyridinyl]-3-(4-piperidinyl)-1-propanone (step 5 in example 9, 110 mg, 0.369 mmol), 1-iodobutane (0.046 ml, 0.406 mmol) and potassium carbonate (102 mg, 0.738 mmol) in tetrahydrofuran (3 ml) was refluxed for 2 h. After cooling to room temperature, the mixture was diluted with ethyl acetate (50 ml), washed with water (5 ml) and brine (10 ml), and dried over potassium carbonate. Removal of solvent gave a pale yellow oil, which was crystallized from methanol to afford 92 mg (64%) of the title compound as a white crystal.

Aufarbeitung

  1. temperaturewas refluxed for 2 h
  2. washwashed with water (5 ml) and brine (10 ml)
  3. dry with materialdried over potassium carbonate
  4. customRemoval of solvent
  5. customgave a pale yellow oil, which
  6. customwas crystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-5d24181a7f964acfb6a49e4e4eb89419
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06979690B2

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