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 1742409Notes

Reaction equation

HRID 1742409 reaction equation
[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]

Participants

4

Reactant 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

Product 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-oneYield 31.2%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-08d3cbea25c941afb3042c365a0933ec
Source dataset
uspto-grants-1994_08
Patent number
US05338740

Reaction notes

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