Azido(trimethyl)stannane → ethyl 1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate

HRID 1760869Notes

Reaction equation

HRID 1760869 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][CH2:28][CH3:29])=[O:26])=[CH:22][CH:23]=[CH:24][C:19]=3[N:18]=[C:17]2[O:30][CH2:31][CH3:32])=[CH:11][CH:10]=1)#[N:2].C[Sn]([N:37]=[N+:38]=[N-:39])(C)C>C1(C)C=CC=CC=1>[CH2:31]([O:30][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:39][N:38]=[N:37][N:2]=3)=[CH:14][CH:13]=2)[C:20]2[C:21]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=1)[CH3:32]

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 15434963Ethyl 1-((2'-cyano(1,1'-biphenyl)-4-yl)methyl)-2-ethoxy-1H-benzimidazole-7-carboxylate

Product 1

HCID 178468771ethyl 1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of ethyl 1-[(2′-cyanobiphenyl-4-yl)methyl]-2-ethoxybenzimidazole-7-carboxylate (0.7 g) and trimethyltin azide (0.7 g) in toluene (15 ml) was heated under reflux for 4 days. The reaction mixture was concentrated to dryness and to the residue were added methanol (20 ml) and 1N-HCl (10 ml). The mixture was stirred at room temperature for 30 minutes and adjusted to pH 3 to 4 with 1N NaOH. After removal of the solvent, the residue was partitioned between chloroform and water. The organic layer was washed with water and dried, and the solvent was evaporated to dryness to give a syrup. The syrup was purified by column chromatography on silica gel to give crystals. Recrystallization from ethyl acetate-benzene afforded colorless crystals (0.35 g, 45%), m.p. 158-159° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 days
  3. concentrationThe reaction mixture was concentrated to dryness and to the residue
  4. additionwere added methanol (20 ml) and 1N-HCl (10 ml)
  5. customAfter removal of the solvent
  6. customthe residue was partitioned between chloroform and water
  7. washThe organic layer was washed with water
  8. customdried
  9. customthe solvent was evaporated to dryness
  10. customto give a syrup
  11. customThe syrup was purified by column chromatography on silica gel
  12. customto give crystals
  13. customRecrystallization from ethyl acetate-benzene afforded colorless crystals (0.35 g, 45%), m.p. 158-159° C.

Sources & evidence

ORD record
ord-41d082c7cb1f446798da6e1213ad64e6
Source dataset
uspto-grants-2005_01
Patent number
US06844443B2

Reaction notes

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