Methyl N-(triethylammoniosulfonyl)carbamate → 5-[5-(4-Allyloxy-3,5-dimethyl-phenyl)-[1,3,4]oxadiazol-2-yl]-2-isobutyl-3-methyl-pyridine

HRID 2065919Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2065919
[CH2:1]([O:4][C:5]1[C:27]([CH3:28])=[CH:26][C:8]([C:9]([NH:11][NH:12][C:13](=O)[C:14]2[CH:19]=[C:18]([CH3:20])[C:17]([CH2:21][CH:22]([CH3:24])[CH3:23])=[N:16][CH:15]=2)=[O:10])=[CH:7][C:6]=1[CH3:29])[CH:2]=[CH2:3].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1.CC(=O)OCC>[CH2:1]([O:4][C:5]1[C:27]([CH3:28])=[CH:26][C:8]([C:9]2[O:10][C:13]([C:14]3[CH:19]=[C:18]([CH3:20])[C:17]([CH2:21][CH:22]([CH3:23])[CH3:24])=[N:16][CH:15]=3)=[N:12][N:11]=2)=[CH:7][C:6]=1[CH3:29])[CH:2]=[CH2:3]

Komponenten

5

Edukt 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 687652896-isobutyl-5-methyl-nicotinic acid N'-(4-allyloxy-3,5-dimethyl-benzoyl)-hydrazide

Produkt 1

HCID 687661605-[5-(4-Allyloxy-3,5-dimethyl-phenyl)-[1,3,4]oxadiazol-2-yl]-2-isobutyl-3-methyl-pyridineAusbeute 94,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 6-isobutyl-5-methyl-nicotinic acid N′-(4-allyloxy-3,5-dimethyl-benzoyl)-hydrazide (89 mg, 0.224 mmol) and Burgess reagent (162 mg, 0.68 mmol) in THF (4 mL) is heated in a microwave oven at 110° C. for 6 min. The mixture is diluted with EA (15 mL) and washed with 1M aq. NaH2PO4 (5 mL), 1M aq. NaOH (5 mL) and water (5 mL). The org. phase is dried (MgSO4), filtered and evaporated to provide crude 5-[5-(4-allyloxy-3,5-dimethyl-phenyl)-[1,3,4]oxadiazol-2-yl]-2-isobutyl-3-methyl-pyridine (80 mg); LC-MS: tR=1.07 min, [M+1]+=378.3.

Aufarbeitung

  1. washwashed with 1M aq. NaH2PO4 (5 mL), 1M aq. NaOH (5 mL) and water (5 mL)
  2. dry with materialphase is dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-c396a6b414cc444eb45d04b282d1d83e
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288554B2

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