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Triethylamine → 3-{5-[(1S,4S)-2-oxa-5-azabicyclo[2.2.1]hept-5-ylmethyl]-1H-tetrazol-1-yl}-5-(trifluoromethyl)benzonitrile

HRID 517786
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 517786
[C@H:1]12[CH2:26][C@H:4]([N:5]([CH2:7][C:8]3[N:12]([C:13]4[CH:14]=[C:15]([CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=4)[C:16]([NH2:18])=O)[N:11]=[N:10][N:9]=3)[CH2:6]1)[CH2:3][O:2]2.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl>[C@H:1]12[CH2:26][C@H:4]([N:5]([CH2:7][C:8]3[N:12]([C:13]4[CH:14]=[C:15]([CH:19]=[C:20]([C:22]([F:23])([F:25])[F:24])[CH:21]=4)[C:16]#[N:18])[N:11]=[N:10][N:9]=3)[CH2:6]1)[CH2:3][O:2]2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydride2×HCID 66656200HCID 66656200, Verbindung2×

Produkt 1

HCID 866919003-{5-[(1S,4S)-2-oxa-5-azabicyclo[2.2.1]hept-5-ylmethyl]-1H-tetrazol-1-yl}-5-(trifluoromethyl)benzonitrileAusbeute 37,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

To a solution of 3-{5-[(1S,4S)-2-oxa-5-azabicyclo[2.2.1]hept-5-ylmethyl]-1H-tetrazol-1-yl}-5-(trifluoromethyl)benzamide (Intermediate 32, 100 mg, 0.272 mmol) and triethylamine (0.076 ml, 0.543 mmol) in dichloromethane (5 ml) was added trifluoroacetic anhydride (0.038 ml, 0.272 mmol). The reaction was stirred at room temperature for 4 hours before the addition of trifluoroacetic anhydride (0.038 ml, 0.272 mmol). The reaction was stirred at room temperature for a further three hours. The reaction was partitioned between DCM (5 mL) and water (5 mL). The organic layer was collected via a hydrophobic frit and the solvent removed. The residue was purified by silica chromatography (Biotage SP4, eluting a gradient from 20-80% EtOAc in iso-hexane). The compound was further purified by high pH MDAP to yield the title compound as a white solid (36 mg)

Aufarbeitung

  1. customThe reaction was partitioned between DCM (5 mL) and water (5 mL)
  2. customThe organic layer was collected via a hydrophobic frit
  3. customthe solvent removed
  4. customThe residue was purified by silica chromatography (Biotage SP4
  5. washeluting a gradient from 20-80% EtOAc in iso-hexane)
  6. customThe compound was further purified by high pH

Quellen und Nachweise

ORD-Eintrag
ord-ee179f7ca84a4347896763ac94b9dc72
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09115132B2

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