Formamidine acetate → HCID 178432631, Verbindung

HRID 1907195Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1907195
FC(F)(F)C(O)=O.[Br:8][C:9]1[N:13]([CH3:14])[N:12]=[CH:11][C:10]=1[C:15]1[N:16]=[C:17]([CH3:21])[N:18]([NH2:20])[CH:19]=1.C(O)(=O)C.[CH:26](N)=[NH:27]>CC(O)CC>[Br:8][C:9]1[N:13]([CH3:14])[N:12]=[CH:11][C:10]=1[C:15]1[N:16]=[C:17]([CH3:21])[N:18]([NH:20][CH:26]=[NH:27])[CH:19]=1

Komponenten

4

Edukt 2

HCID 160693Formamidine acetateHCID 1317310614-(5-bromo-1-methyl-1H-pyrazol-4-yl)-2-methyl-1H-imidazol-1-amine, trifluoroacetate salt

Produkt 1

HCID 178432631HCID 178432631, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6568(+-)-2-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

4-(5-Bromo-1-methyl-1H-pyrazol-4-yl)-2-methyl-1H-imidazol-1-amine, trifluoroacetate salt (4.90 g, 113.2 mmol) was combined with formamidine acetate (98%, 4.92 g, 46.3 mmol) in 2-butanol (40 mL), and the reaction mixture was heated at 100° C. for 6 hours, then allowed to cool to room temperature and stir for 18 hours. The off-white solid was collected by filtration and washed with 2-propanol followed by diethyl ether. The solid was then triturated with aqueous ammonium hydroxide (7.5 M, 40 mL); filtration provided a white solid, which was washed with 2-propanol followed by diethyl ether to provide the product. Yield: 2.70 g, 9.54 mmol, 72%. 1H NMR (500 MHz, CD3OD), presumed to be a mixture of rotamers or tautomers: δ 2.26 and 2.31 (2 s, 3H), 3.89 and 3.89 (2 s, 3H), 7.26 and 7.40 (2 s, 1H), 7.41 and 7.96 (2 br s, 1H), 7.85 and 7.82 (2 s, 1H).

Aufarbeitung

  1. temperatureto cool to room temperature
  2. filtrationThe off-white solid was collected by filtration
  3. washwashed with 2-propanol
  4. customThe solid was then triturated with aqueous ammonium hydroxide (7.5 M, 40 mL)
  5. filtrationfiltration
  6. customprovided a white solid, which
  7. washwas washed with 2-propanol
  8. customto provide the product
  9. additiona mixture of rotamers or tautomers
  10. customδ 2.26 and 2.31 (2 s, 3H), 3.89 and 3.89 (2 s, 3H), 7.26 and 7.40 (2 s, 1H), 7.41 and 7.96 (2 br s, 1H), 7.85 and 7.82 (2 s, 1H)

Quellen und Nachweise

ORD-Eintrag
ord-7fd1be415d40403887c1bf8ad874eee3
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598155B2

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