Isobutylamine → N-(isobutyl)-2-(2-(phenylsulfonyl)ethylthio)nicotinamide

HRID 660064Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 660064
C1N=CN(C(N2C=NC=C2)=O)C=1.[C:13]1([S:19]([CH2:22][CH2:23][S:24][C:25]2[N:33]=[CH:32][CH:31]=[CH:30][C:26]=2[C:27]([OH:29])=O)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH2:34]([NH2:38])[CH:35]([CH3:37])[CH3:36]>C(Cl)Cl.C(OCC)(=O)C>[CH2:34]([NH:38][C:27](=[O:29])[C:26]1[CH:30]=[CH:31][CH:32]=[N:33][C:25]=1[S:24][CH2:23][CH2:22][S:19]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)(=[O:20])=[O:21])[CH:35]([CH3:37])[CH3:36]

Komponenten

6

Edukt 3

HCID 6558IsobutylamineHCID 682631,1'-CarbonyldiimidazoleHCID 28213502-[2-(Phenylsulfonyl)ethylthio]nicotinic acid

Produkt 1

HCID 68745486N-(isobutyl)-2-(2-(phenylsulfonyl)ethylthio)nicotinamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

171 mg (1.05 mmol) of CDI were added to a solution of 323 mg (1.00 mmol) of 2-(2-(phenylsulfonyl)ethylthio)nicotinic acid in DCM (16 ml), and the mixture was stirred for 1 hour at RT. 99 μl (1.00 mmol) of isobutylamine were then added, and stirring was continued for a further 5 days at RT. The reaction solution was then washed in each case twice with a 4 M aq. ammonium chloride solution and a 1 M aq. sodium hydrogen carbonate solution. The organic phase was dried over MgSO4, filtered and concentrated in vacuo. The residue obtained was taken up in ethyl acetate (30 ml) and washed with 0.4 M hydrochloric acid (5 ml). The organic phase was again dried over MgSO4, filtered and concentrated in vacuo. 160 mg (0.42 mmol, 42 of N-(isobutyl)-2-(2-(phenylsulfonyl)ethylthio)nicotinamide were obtained as residue. MS: m/z 379.1 [M+H]+

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for a further 5 days at RT
  3. washThe reaction solution was then washed in each case twice with a 4 M aq. ammonium chloride solution
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue obtained
  8. washwashed with 0.4 M hydrochloric acid (5 ml)
  9. dry with materialThe organic phase was again dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-376cee0168bb47cf8449a3967450de1e
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084470B2

Notizen zur Reaktion

Wird geladen…