Azido(trimethyl)stannane → HCID 178467365, compound

HRID 494359Notes

Reaction equation

HRID 494359 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:20]3[C:21]([C:25]([O:27][CH3:28])=[O:26])=[CH:22][CH:23]=[CH:24][C:19]=3[N:18]=[C:17]2[O:29][CH2:30][CH3:31])=[CH:11][CH:10]=1)#[N:2].C[Sn]([N:36]=[N+:37]=[N-:38])(C)C>C1(C)C=CC=CC=1>[CH2:30]([O:29][C:17]1[N:16]([CH2:15][C:12]2[CH:11]=[CH:10][C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[C:1]3[NH:38][N:37]=[N:36][N:2]=3)=[CH:14][CH:13]=2)[C:20]2[C:21]([C:25]([O:27][CH3:28])=[O:26])=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=1)[CH3:31]

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 15654674Methyl 1-[(2'-cyano[1,1'-biphenyl]-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate

Product 1

HCID 178467365HCID 178467365, compoundYield 56.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl 1-[(2′-cyanobiphenyl-4-yl)methyl]-2-ethoxybenzimidazole-7-carboxylate (1.85 g) and trimethyltin azide (2.80 g) in toluene (15 ml) were heated under reflux for one day. The reaction mixture was concentrated to dryness. To the residue were added methanol (50 ml) and 1N-HCl (20 ml) and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was adjusted to about pH 3-4 with 1N-NaOH. After removal of the solvent, the residual syrup was purified by column chromatography on silica gel to give crystals. Recrystallization from ethyl acetate-benzene gave colorless crystals (1.16 g, 56%), m.p. 191-193° C. (decomp.).

Workup

  1. temperaturewere heated
  2. temperatureunder reflux for one day
  3. concentrationThe reaction mixture was concentrated to dryness
  4. additionTo the residue were added methanol (50 ml) and 1N-HCl (20 ml)
  5. customAfter removal of the solvent
  6. customthe residual syrup was purified by column chromatography on silica gel
  7. customto give crystals
  8. customRecrystallization from ethyl acetate-benzene

Sources & evidence

ORD record
ord-65a345dadf13498b984abe99636c3b0f
Source dataset
uspto-grants-2009_05
Patent number
US07538133B2

Reaction notes

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