Diisopropylethylamine → 8-Bromo-(1,2,4)triazolo(1,5-a)pyridin-2-amine

HRID 57763

Reaktionsgleichung

Reaktionsgleichung von HRID 57763
Cl.NO.C([N:7](CC)C(C)C)(C)C.[Br:13][C:14]1[C:15]([NH:20][C:21]([NH:23]C(=O)OCC)=S)=[N:16][CH:17]=[CH:18][CH:19]=1>CO.C(O)C>[Br:13][C:14]1[C:15]2[N:16]([N:7]=[C:21]([NH2:23])[N:20]=2)[CH:17]=[CH:18][CH:19]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 59199107Ethyl aminon-(3-bromopyridin-2-YL)methanethiocarbamate

Produkt 1

HCID 468640698-Bromo-(1,2,4)triazolo(1,5-a)pyridin-2-amineAusbeute 40.466,102 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 18681192Ethanol, mixt. with methanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of hydroxylamine hydrochloride (0.10 kg, 1.4 mol, 5.0 equiv) and N,N-diisopropylethylamine (112 g, 0.867 mol, 3.00 eq) in 1:1 methanol/ethanol (1.5 L) was added ethyl [(3-bromopyridin-2-yl)carbamothioyl]carbamate (88 g, 0.29 mmol, 1 equiv) in one portion at room temperature. After 2 h, the reaction mixture was warmed to 60° C. for overnight. The reaction mixture was concentrated in vacuo, and water was added to the resulting residue. The solids were filtered and rinsed sequentially with 4:1 methanol/diethyl ether and diethyl ether to provide product as an off-white solid (25 g, 40%). LCMS (ESI) m/z: 212.8; 1H NMR (400 MHz, DMSO-d6) δ: 8.55 (m 1H), 7.70 (m, 1H), 6.75 (m, 1H), 6.20 (br s, 2H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo, and water
  2. additionwas added to the resulting residue
  3. filtrationThe solids were filtered
  4. washrinsed sequentially with 4:1 methanol/diethyl ether and diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-3745708aa5114b139119a7c422ec1767
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434732B2

Verknüpfte Notizen

Wird geladen…