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Triethylamine → 8-({1-[3-(Trifluoromethyl)phenyl]-1H-tetrazol-5-yl}methyl)-2,8-diazaspiro[4.5]decan-1-one

HRID 517756
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 517756
Cl[CH2:2][C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[N:6]=[N:5][N:4]=1.Cl.[C:19]1(=[O:29])[C:23]2([CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH2:22][CH2:21][NH:20]1.C(N(CC)CC)C>C(#N)C>[F:15][C:14]([F:17])([F:16])[C:10]1[CH:9]=[C:8]([N:7]2[C:3]([CH2:2][N:26]3[CH2:27][CH2:28][C:23]4([C:19](=[O:29])[NH:20][CH2:21][CH2:22]4)[CH2:24][CH2:25]3)=[N:4][N:5]=[N:6]2)[CH:13]=[CH:12][CH:11]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 80271755-(Chloromethyl)-1-(3-(trifluoromethyl)phenyl)-1H-tetrazoleHCID 426145582,8-Diazaspiro(4.5)decan-1-one hydrochloride

Produkt 1

HCID 866918858-({1-[3-(Trifluoromethyl)phenyl]-1H-tetrazol-5-yl}methyl)-2,8-diazaspiro[4.5]decan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342Acetonitrile
Lösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of 5-(chloromethyl)-1-[3-(trifluoromethyl)phenyl]-1H-tetrazole (200 mg, 0.762 mmol, commercially available from Otava, Kiev, Ukraine) in acetonitrile (4 mL) was added 2,8-diazaspiro[4.5]decan-1-one hydrochloride (290 mg, 1.52 mmol, Tyger Scientific, Ewing, USA) and triethylamine (0.318 mL, 2.29 mmol). The reaction mixture was heated at 120° C. for 20 minutes in a microwave reactor. The reaction mixture was then cooled and the solvent removed under vacuum. The residue was purified by MDAP. Fractions containing the desired product were combined and the solvent removed. The product was partitioned between DCM (6 mL) and saturated aqueous NaHCO3 (3 mL) and the organic layer collected via a hydrophobic frit. The solvent was removed under a stream of argon to yield the title compound as a solid (0.161 g).

Aufarbeitung

  1. temperatureThe reaction mixture was then cooled
  2. customthe solvent removed under vacuum
  3. customThe residue was purified by MDAP
  4. additionFractions containing the desired product
  5. customthe solvent removed
  6. customThe product was partitioned between DCM (6 mL) and saturated aqueous NaHCO3 (3 mL)
  7. customthe organic layer collected via a hydrophobic frit
  8. customThe solvent was removed under a stream of argon

Quellen und Nachweise

ORD-Eintrag
ord-c8ee20792b434d7182d52478267d2934
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09115132B2

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