Diisopropylethylamine → 2-Amino-5-chloro-4-(4-(5-methyl-1,2,4-oxadiazol-3-yl)methylpiperazin-1-yl)-3-nitropyridine

HRID 63593

Reaktionsgleichung

Reaktionsgleichung von HRID 63593
Cl.[CH3:2][C:3]1[O:7][N:6]=[C:5]([CH2:8][N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[N:4]=1.[NH2:15][C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[C:20](Cl)[C:19]([Cl:26])=[CH:18][N:17]=1.C(N(C(C)C)CC)(C)C>CC(O)C>[NH2:15][C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[C:20]([N:12]2[CH2:11][CH2:10][N:9]([CH2:8][C:5]3[N:4]=[C:3]([CH3:2])[O:7][N:6]=3)[CH2:14][CH2:13]2)[C:19]([Cl:26])=[CH:18][N:17]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 468676602-Amino-4,5-dichloro-3-nitropyridineHCID 755306881-[(5-Methyl-1,2,4-oxadiazol-3-yl)methyl]piperazine hydrochloride

Produkt 1

HCID 714814732-Amino-5-chloro-4-(4-(5-methyl-1,2,4-oxadiazol-3-yl)methylpiperazin-1-yl)-3-nitropyridineAusbeute 70,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

1-[(5-Methyl-1,2,4-oxadiazol-3-yl)methyl]piperazine hydrochloride (217 mg, 0.99 mmol) and 2-amino-4,5-dichloro-3-nitropyridine (208 mg, 1.0 mmol) were stirred in 2-propanol (5 mL) and diisopropylethylamine (523 μL, 387 mg, 3.0 mmol) was added. The mixture was stirred and heated at 45° C. for 23 h. The reaction was cooled and the product filtered off and washed with 2-propanol. Drying in vacuum gave the product (246 mg, 69%). 1H-NMR (500 MHz, CDCl3), 2.63 (s, 3H, CH3), 2.77 (br m, 4H, piperazine C—H), 3.29 (m, 4H, piperazine C—H), 3.76 (s, 2H, CH2), 5.27 (s, 2H, NH2), 8.02 (s, 1H, pyridine 6-H).

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. filtrationthe product filtered off
  3. washwashed with 2-propanol
  4. customDrying in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-ca11d6524ce540f6b793af1492dd8c08
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447092B2

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