4-(Bromomethyl)benzoic acid → 5-Bromo-3-(5-(4-(bromomethyl)phenyl)-1,3,4-oxadiazol-2-yl)pyrazin-2-amine

HRID 78670

Reaktionsgleichung

Reaktionsgleichung von HRID 78670
BrP(Br)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Br:22][CH2:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([OH:30])=O)=[CH:26][CH:25]=1.[NH2:33][C:34]1[C:35]([C:41]([NH:43][NH2:44])=O)=[N:36][C:37]([Br:40])=[CH:38][N:39]=1.CCN(C(C)C)C(C)C>C(#N)C>[Br:40][C:37]1[N:36]=[C:35]([C:41]2[O:30][C:28]([C:27]3[CH:26]=[CH:25][C:24]([CH2:23][Br:22])=[CH:32][CH:31]=3)=[N:44][N:43]=2)[C:34]([NH2:33])=[N:39][CH:38]=1

Komponenten

6

Edukt 4

HCID 225994-(Bromomethyl)benzoic acidHCID 70579Triphenylphosphine dibromideHCID 81531Diisopropylethylamine2×HCID 580702563-Amino-6-bromopyrazine-2-carbohydrazide

Produkt 1

HCID 580704675-Bromo-3-(5-(4-(bromomethyl)phenyl)-1,3,4-oxadiazol-2-yl)pyrazin-2-amineAusbeute 66,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Dibromo(triphenyl)phosphorane (37.29 g, 88.35 mmol) was added to a suspension of 4-(bromomethyl)benzoic acid (4.318 g, 20.08 mmol) and 3-amino-6-bromo-pyrazine-2-carbohydrazide (4.66 g, 20.08 mmol) in acetonitrile (143.4 mL). The resulting mixture was stirred at room temperature for 2 h and then Hunig's base (15.57 g, 20.98 mL, 120.5 mmol) was added and the reaction was stirred overnight. Exotherm observed during Hunig's base addition; moderated with ice bath (temp. kept around 20+/−4). The reaction mixture was filtered and the solid obtained washed with cold acetonitrile to leave the product as a yellow solid (5.45 g, 66.7% yield); 1H NMR (400.0 MHz, DMSO) d 4.82 (s, 2H), 7.72 (d, 2H), 7.80 (s, 1H), 8.11 (d, 2H) and 8.45 (s, 1H) ppm; MS (ES+) 412.1.

Aufarbeitung

  1. stirringthe reaction was stirred overnight
  2. filtrationThe reaction mixture was filtered
  3. customthe solid obtained
  4. washwashed with cold acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-9a42558b8bd74c76acf8ab128b491d43
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841308B2

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