1-Heptanamine → 5-(4,5-diphenyl-1H-imidazol-2-ylthio)-N-heptylpentanamide

HRID 374045Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 374045
[C:1]1([C:7]2[N:8]=[C:9]([S:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=O)[NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.ON1C2C=CC=CC=2N=N1.[CH2:37]([NH2:44])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[C:1]1([C:7]2[N:8]=[C:9]([S:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([NH:44][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])=[O:25])[NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

6

Edukt 4

HCID 81271-HeptanamineHCID 10868DicyclohexylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 189587125-[(4,5-Diphenyl-1H-imidazol-2-YL)sulfanyl]pentanoic acid

Produkt 1

HCID 28177995-(4,5-diphenyl-1H-imidazol-2-ylthio)-N-heptylpentanamideAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Part C, Method 1. To a solution of 5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentanoic acid (2.0 g, 0.0057 mol) in N,N-dimethylformamide (25 mL) was added 1-hydroxybenzotriazole hydrate (0.93 g, 0.0069 mol) followed by a solution of heptylamine (1.10 mL, 0.86 g, 0.0074 mol) in N,N-dimethylformamide (10 mL). The reaction mixture was cooled to 0° and dicyclohexylcarbodiimide (1.42 g, 0.0069 mol) was added portionwise as a solid. The reaction mixture was stirred for 2 hours at 0° and then stirred for 48 hours at ambient temperature. The solids were filtered and washed with N,N-dimethylformamide. The filtrate was concentrated and the residue was chromatographed with 1:1 hexane-ethyl acetate. The resulting solid was recrystallized from acetonitrile and triturated with hexane to give 5-(4,5-diphenyl-1H-imidazol-2-ylthio)-N-heptylpentanamide (2.21 g, 0.0049 mol) as a white solid, mp 104°-106°. 1H NMR (CDCl3) δ11.6(s,1H), 7.6-7.1(m,10H), 6.1-6.0(m,1H), 3.1-2.8(m,4H), 2.2(t,2H,J=7Hz), 1.9-1.7(m,2H), 1.7-1.5(m,2H), 1.4-1.1(m,10H), 0.9(t,3H,J=8Hz).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to 0°
  2. stirringstirred for 48 hours at ambient temperature
  3. filtrationThe solids were filtered
  4. washwashed with N,N-dimethylformamide
  5. concentrationThe filtrate was concentrated
  6. customthe residue was chromatographed with 1:1 hexane-ethyl acetate
  7. customThe resulting solid was recrystallized from acetonitrile
  8. customtriturated with hexane

Quellen und Nachweise

ORD-Eintrag
ord-536eba3ea3654f6da17de6a80ea2cc2f
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05166214

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