Azido(trimethyl)stannane → 2-Butyl-3-{5-[2-(1H-tetrazol-5-yl)-phenyl]-indan-1-yl}-1,3-diaza-spiro[4.4]non-1-en-4-one

HRID 1742409Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1742409
[CH2:1]([C:5]1[N:9]([CH:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]4[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=4[C:21]#[N:22])=[CH:16][CH:17]=3)[CH2:12][CH2:11]2)[C:8](=[O:27])[C:7]2([CH2:31][CH2:30][CH2:29][CH2:28]2)[N:6]=1)[CH2:2][CH2:3][CH3:4].C[Sn]([N:36]=[N+:37]=[N-:38])(C)C>C1(C)C(C)=CC=CC=1>[CH2:1]([C:5]1[N:9]([CH:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]4[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=4[C:21]4[NH:38][N:37]=[N:36][N:22]=4)=[CH:16][CH:17]=3)[CH2:12][CH2:11]2)[C:8](=[O:27])[C:7]2([CH2:28][CH2:29][CH2:30][CH2:31]2)[N:6]=1)[CH2:2][CH2:3][CH3:4]

Komponenten

4

Edukt 2

HCID 5104973Azido(trimethyl)stannaneHCID 190089202-[1-(2-Butyl4-oxo-1,3-diaza-spiro[4.4]non-1-en-3-yl)-indan-5-yl]-benzonitrile

Produkt 1

HCID 1784414412-Butyl-3-{5-[2-(1H-tetrazol-5-yl)-phenyl]-indan-1-yl}-1,3-diaza-spiro[4.4]non-1-en-4-oneAusbeute 31,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

A mixture of 2-[1-(2-butyl-4-oxo-1,3-diaza-spiro[4.4]non-1-en-3-yl)-indan -5yl]-benzonitrile (150 mg, 0.36 mmol) and trimethyltin azide (196 mg, 0.91 mmol) was heated under reflux in xylene (5.0 mL) for 25 hours. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was chromatographed on SiO2 -gel using a gradient of 2.5% MeOH/CH2Cl2 to 10% MeOH/CH2Cl2 to give 51 mg of a colorless oil. The oil was dissolved in EtOAc and hexanes were added to precipitate the product. The white solid was filtered and dried. 1H NMR (250 MHz, d4 -MeOH): d 7.58 (m, 2 H), 7.47 (m, 2 H), 7.00 (s, 1 H), 6.85 (s, 2 H), 5.50 (t, 1 H), 2.95 (m, 2 H), 2.35 (m, 4 H), 1.90-1.41 (m), 1.22 (m, 2 H), 0.80 (t, 3 H).

Aufarbeitung

  1. temperaturewas heated
  2. concentrationconcentrated in vacuo
  3. customThe residue was chromatographed on SiO2

Quellen und Nachweise

ORD-Eintrag
ord-08d3cbea25c941afb3042c365a0933ec
Quelldatensatz
uspto-grants-1994_08
Patentnummer
US05338740

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