Triethylamine → N-[5-[(E)-N'-hydroxycarbamimidoyl]-2-pyridinyl]-3,5-bis(phenylmethoxy)benzamide

HRID 552609Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 552609
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:23]=[C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:25]=1)[C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][N:16]=1)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl.[NH2:42][OH:43]>C(O)C>[CH2:27]([O:26][C:24]1[CH:23]=[C:11]([CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:25]=1)[C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([NH:42][OH:43])=[NH:22])=[CH:17][N:16]=1)=[O:13])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 230729493,5-bis(benzyloxy)-N-(5-cyanopyridin-2-yl)benzamide

Produkt 1

HCID 178513344N-[5-[(E)-N'-hydroxycarbamimidoyl]-2-pyridinyl]-3,5-bis(phenylmethoxy)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 3,5-bis(benzyloxy)-N-(5-cyanopyridin-2-yl)benzamide (212 mg, 0.49 mmol), triethylamine (170 μL, 1.22 mmol) and hydroxylamine hydrochloride (85 mg, 1.22 mmol) in ethanol (5 mL) was heated at reflux overnight. The mixture was cooled and concentrated under reduced pressure. The residue was purified by MPLC on silica eluting with 5% methanol/DCM then 15% methanol/DCM. The title compound was obtained as a colourless solid (171 mg, 75%). 1H NMR δ (d6-DMSO): 5.19 (4H, s); 5.92 (2H, s), 6.87 (1H, s); 7.28-7.48 (12H, m); 8.06 (1H, dd); 8.17 (1H, d), 8.65 (1H, s); 9.68 (1H, s); 10.85 (1H, br s); m/z (LCMS; ESI+) 469 (MH+).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by MPLC on silica eluting with 5% methanol/DCM

Quellen und Nachweise

ORD-Eintrag
ord-f198ca05def7445cacb41c70095c7dc3
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07951830B2

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