Pyridine → 4-chlorobutyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenylmethylidene]amino]oxymethyl]-2-pyridinyl]carbamate

HRID 1914612Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1914612
[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.N1C=CC=CC=1.[C:30](Cl)(=[O:37])[O:31][CH2:32][CH2:33][CH2:34][CH2:35][Cl: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:30](=[O:37])[O:31][CH2:32][CH2:33][CH2:34][CH2:35][Cl: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 1049PyridineHCID 27333284-Chlorobutyl carbonochloridateHCID 768322206-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-amine

Produkt 1

HCID 1405662204-chlorobutyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenylmethylidene]amino]oxymethyl]-2-pyridinyl]carbamateAusbeute 92,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)-methyl]pyridin-2-amine (150 mg, 0.485 mmol) in dichloromethane (5 mL), was added pyridine (0.078 mL), 4-chlorobutyl carbonochloridate (166 mg, 0.970 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 4-chlorobutyl {6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate [200 mg; 90% of purity; 84% of to theory; HPLC/MS: m/z=344 (M+H); log P(HCOOH)=3.67].

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-114569c88ec64124a8a5a13f1df7fb10
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08614217B2

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