Diisopropylethylamine → 4-(3-amino-2,2-difluoropropylamino)-4-methyl-1-(2-nitro-1H-imidazol-1-yl)-3-pentanone oxime

HRID 2293902Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2293902
Cl.Cl.[NH2:3][CH2:4][C:5]([F:9])([F:8])[CH2:6][NH2:7].C(N(CC)C(C)C)(C)C.Cl[C:20]([CH3:35])([CH3:34])[CH:21]([N:32]=[O:33])[CH2:22][CH2:23][N:24]1[CH:28]=[CH:27][N:26]=[C:25]1[N+:29]([O-:31])=[O:30]>C(#N)C>[NH2:3][CH2:4][C:5]([F:9])([F:8])[CH2:6][NH:7][C:20]([CH3:35])([CH3:34])[C:21](=[N:32][OH:33])[CH2:22][CH2:23][N:24]1[CH:28]=[CH:27][N:26]=[C:25]1[N+:29]([O-:31])=[O:30]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 151859944-chloro-4-methyl-1-(2-nitro-1H-imidazol-1-yl)-3-nitrosopentaneHCID 222877692,2-Difluoropropane-1,3-diamine dihydrochloride

Produkt 1

HCID 738801844-(3-amino-2,2-difluoropropylamino)-4-methyl-1-(2-nitro-1H-imidazol-1-yl)-3-pentanone oxime

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a mixture of 1,3-diamino-2,2-difluoropropane dihydrochloride (title A diamine) (1.10 g, 6.01 mmol) and N,N-diisopropylethylamine (2.72 g, 21.04 mmol) in acetonitrile (10 mL) at 40° C. was added 4-chloro-4-methyl-1-(2-nitro-1H-imidazol-1-yl)-3-nitrosopentane (Example 3, step (B)) (0.50 g, 1.90 mmol) in small portions with 30 stirring under nitrogen atmosphere. After the addition, the stirring was continued for an additional 30 minutes and the solvent was removed on a rotary evaporator. The paste obtained was treated with silica gel and the silica gel powder impregnated with the compound was loaded onto a silica gel column and eluted with CH3OH--CH2Cl2 (5:95). The fractions containing compound were collected and evaporated to give the title product as a light yellow colored solid. Yield: 0.42 g (66%), mp. 112°-114° C.; 1H NMR (CDCl3) d 1.19 [s, 6H, C(CH3)2 ], 2.88 [m, 4H, C(=N)CH2 & NHCH2 ], 3.71 (t, 3H, JHF =13.19 Hz, CH2NH2), 4.72 (t, 2H, J=7.26, CH2CH2N), 7.11 & 7.26 (2s, 2H, nitroimid-H) and 10.79 (s, 1H, NOH). MS m/e 335 (M+H)+.

Aufarbeitung

  1. additionAfter the addition
  2. customthe solvent was removed on a rotary evaporator
  3. customThe paste obtained
  4. additionwas treated with silica gel
  5. washeluted with CH3OH--CH2Cl2 (5:95)
  6. additionThe fractions containing compound
  7. customwere collected
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-987550dc1c094edbb88d075f8b37a6ab
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05688487

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