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Methanol → tert-butyl 4-[5-(6-methoxypyridin-3-yl)-4H-1,2,4-triazol-3-yl]piperidine-1-carboxylate

HRID 605014
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 605014
[NH:1]([C:3]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)=O)[NH2:2].CO[C:20]1[CH:21]=[C:22]([C:26]#[N:27])[CH:23]=[N:24][CH:25]=1.[CH3:28][O-:29].[Na+].CO>C(OCCO)C.C(O)(=O)C>[CH3:28][O:29][C:25]1[N:24]=[CH:23][C:22]([C:26]2[NH:27][C:3]([CH:5]3[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]3)=[N:1][N:2]=2)=[CH:21][CH:20]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 22713165tert-Butyl 4-(hydrazinecarbonyl)piperidine-1-carboxylateHCID 231597785-Methoxypyridine-3-carbonitrile

Produkt 1

HCID 178489121tert-butyl 4-[5-(6-methoxypyridin-3-yl)-4H-1,2,4-triazol-3-yl]piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176
Acetic Acid
Lösungsmittel
HCID 8076Glycol monoethyl etherLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

tert-Butyl 4-(hydrazinocarbonyl)-piperidine-1-carboxylate (800 mg, 3.29 mmol) was dissolved in anhydrous 2-ethoxyethanol (10 mL) and 5-methoxypyridine-3-carbonitrile (662 mg, 4.9 mmol) was added to the solution. A solution of 0.5M sodium methoxide in methanol (3 mL, ˜1.5 mmol) was added and the mixture was heated at 130° C. for 16 h. The cooled reaction mixture was neutralized with acetic acid and partitioned between ethyl acetate and aq. NaHCO3. The organic layer was dried over Na2SO4, the salts removed by filtration and the solvent evaporated under vacuum. This residue was triturated with diethyl ether to give tert-butyl 4-[5-(6-methoxypyridin-3-yl)-4H-1,2,4-triazol-3-yl]piperidine-1-carboxylate as a white solid. This material was dissolved in methylene chloride (10 mL) and TFA (10 mL) was added. After one hour the solvent was evaporated under reduced pressure to give 2-methoxy-5-(5-piperidin-4-yl-4H-1,2,4-triazol-3-yl)pyridine. NMR (MeOD): δ 8.75 (1H, s), 8.19 (1H, d, J=6 Hz), 6.93 (1H, d, J=6 Hz), 3.95 (3H, s), 3.51 (2H, m), 3.22 (3H, m), 2.32 (2H, m), 2.11 (2H, m).

Aufarbeitung

  1. customThe cooled reaction mixture
  2. custompartitioned between ethyl acetate and aq. NaHCO3
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customthe salts removed by filtration
  5. customthe solvent evaporated under vacuum
  6. customThis residue was triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-07bdc3c61365467cab3a7c1749673ca9
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07910561B2

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