Azido(trimethyl)stannane → HCID 178439912, compound

HRID 1586837Notes

Reaction equation

[C:1]([C:3]1[O:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH:27]=[CH:26][C:11]([CH2:12][N:13]2[C:17]3=[N:18][CH:19]=[CH:20][C:21]([CH3:22])=[C:16]3[N:15]=[C:14]2[CH2:23][CH2:24][CH3:25])=[CH:10][CH:9]=1)#[N:2].C[Sn]([N:32]=[N+:33]=[N-:34])(C)C>C1(C)C(C)=CC=CC=1>[CH3:22][C:21]1[CH:20]=[CH:19][N:18]=[C:17]2[N:13]([CH2:12][C:11]3[CH:10]=[CH:9][C:8]([C:7]4[CH:6]=[CH:5][O:4][C:3]=4[C:1]4[NH:34][N:33]=[N:32][N:2]=4)=[CH:27][CH:26]=3)[C:14]([CH2:23][CH2:24][CH3:25])=[N:15][C:16]=12

Participants

Conditions

Temperature: 125 °C

Procedure

A mixture of 3-[4-(2-cyano-3-furyl)benzyl]-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine (540 mg) and trimethyltin azide (1.095 g) in xylene (10 ml) was stirred at 125° C. for 24 hours. The mixture was concentrated in vacuo. The residue was dissolved in methanol (15 ml) and the methanolic solution was treated with 8.9N methanolic hydrogen chloride (1 ml) for one hour at ambient temperature. The mixture was adjusted to pH 5 with aqueous 1N sodium hydroxide solution and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (elution by dichloromethane/methanol=15/1-8/1) to yield 7-methyl-2-propyl-3-[4-[2-(1H-tetrazol-5-yl)-3-furyl]benzyl]-3H-imidazo[4,5-b]pyridine (525 mg) as an amorphous solid.

Workup

concentrationThe mixture was concentrated in vacuo
dissolutionThe residue was dissolved in methanol (15 ml)
additionthe methanolic solution was treated with 8.9N methanolic hydrogen chloride (1 ml) for one hour at ambient temperature
concentrationconcentrated in vacuo
customThe residue was purified by flash column chromatography on silica gel (elution by dichloromethane/methanol=15/1-8/1)

Sources & evidence

ORD record: ord-04c6e52b93824240ad941fa3772a926f
Source dataset: uspto-grants-1993_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05215994

Reaction notes

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