Triethylamine → N-{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}hex-5-ynamide

HRID 1914608

Reaktionsgleichung

Reaktionsgleichung von HRID 1914608
[CH3:1][N:2]1[C:6]([C:7](=[N:14][O:15][CH2:16][C:17]2[N:22]=[C:21]([NH2:23])[CH:20]=[CH:19][CH:18]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:5][N:4]=[N:3]1.C(N(CC)CC)C.[C:31](Cl)(=[O:37])[CH2:32][CH2:33][CH2:34][C:35]#[CH:36]>ClCCl>[CH3:1][N:2]1[C:6]([C:7](=[N:14][O:15][CH2:16][C:17]2[N:22]=[C:21]([NH:23][C:31](=[O:37])[CH2:32][CH2:33][CH2:34][C:35]#[CH:36])[CH:20]=[CH:19][CH:18]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[N:5][N:4]=[N:3]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 2759284Hex-5-ynoyl chlorideHCID 768322206-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-amine

Produkt 1

HCID 86656569N-{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}hex-5-ynamideAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-amine (251 mg, 0.81 mmol) in dichloromethane (10 mL) was added triethylamine (0.22 mL, 1.62 mmol), hex-5-ynoyl chloride (211 mg, 1.62 mmol). The reaction mixture was stirred for 5 hours at room temperature, concentrated in vacuo, and then purified by silica gel chromatography to yield to N-{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}hex-5-ynamide [200 mg; 95% of purity; 58% of theory; HPLC/MS: m/z=404 (M+H); log P(HCOOH)=2.98].

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. custompurified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3c88f41a314d40ac9e6eb223c5d6b951
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08614217B2

Verknüpfte Notizen

Wird geladen…