Triethylamine → 2-Methyl-4-(6-phenylethynyl-pyridazin-3-ylamino)-butan-2-ol

HRID 1894257

Reaktionsgleichung

Reaktionsgleichung von HRID 1894257
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:7]=1.Cl.[NH2:17][CH2:18][CH2:19][C:20]([CH3:23])([OH:22])[CH3:21].C(N(CC)CC)C>N1C=CC=CC=1>[CH3:21][C:20]([OH:22])([CH2:19][CH2:18][NH:17][C:2]1[N:3]=[N:4][C:5]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:7]=1)[CH3:23]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 126802603-Chloro-6-(phenylethynyl)pyridazineHCID 426145604-Amino-2-methylbutan-2-ol hydrochloride

Produkt 1

HCID 575167752-Methyl-4-(6-phenylethynyl-pyridazin-3-ylamino)-butan-2-olAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A solution of 3-chloro-6-(phenylethynyl)pyridazine (CAS 77778-15-5) (125 mg, 0.582 mmol) and 4-amino-2-methylbutan-2-ol hydrochloride (244 mg, 1.75 mmol, 3 equiv.) and triethylamine (206 mg, 284 ml, 2.04 mmol, 2 equiv.) in 1.25 ml of pyridine was heated 20 hours at 85° C. The solvent was removed in vacuo. The residue was taken up in ethyl acetate/methanol, adsorbed onto 4 g of silica and purified on a 20 g flash chromatography column using a heptane/ethyl acetate 85:15 to 15:85 gradient to yield 44 mg (27% yield) of the title compound as a crystalline white solid, MS: m/e=282.2 (M+H+).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. custompurified on a 20 g flash chromatography column

Quellen und Nachweise

ORD-Eintrag
ord-bb903643330642b69518ce094753364d
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08513273B2

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