Stannous chloride dihydrate → methyl 3-amino-2-(((2'-(1-(4-methoxybenzyl)-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)amino)benzoate

HRID 41797

Reaction equation

HRID 41797 reaction equation
[CH3:1][O:2][C:3]1[CH:41]=[CH:40][C:6]([CH2:7][N:8]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]3[CH:24]=[CH:23][C:22]([CH2:25][NH:26][C:27]4[C:36]([N+:37]([O-])=O)=[CH:35][CH:34]=[CH:33][C:28]=4[C:29]([O:31][CH3:32])=[O:30])=[CH:21][CH:20]=3)=[N:11][N:10]=[N:9]2)=[CH:5][CH:4]=1.O.O.[Sn](Cl)Cl>CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]3[CH:24]=[CH:23][C:22]([CH2:25][NH:26][C:27]4[C:36]([NH2:37])=[CH:35][CH:34]=[CH:33][C:28]=4[C:29]([O:31][CH3:32])=[O:30])=[CH:21][CH:20]=3)=[N:11][N:10]=[N:9]2)=[CH:40][CH:41]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 69916865methyl 2-(((2'-(1-(4-methoxybenzyl)-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)amino)-3-nitrobenzoate2×

Product 1

HCID 69916872methyl 3-amino-2-(((2'-(1-(4-methoxybenzyl)-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)amino)benzoateYield 75.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 2-[({2′-[1-(p-methoxybenzyl)-1H-tetrazol-5-yl]biphenyl-4-yl}methyl)amino]-3-nitrobenzoate (compound 21a, 2.73 g, 4.96 mmol) and tin(II) chloride dihydrate (4.48 g, 19.9 mmol) in methanol (60 mL) was heated under reflux for 2 hr. The reaction mixture was concentrated under reduced pressure, and to the concentrated residue were added saturated aqueous sodium hydrogen carbonate and ethyl acetate. The mixture was stirred for 1 hr, and filtered, and the insoluble material was washed with ethyl acetate. The filtrate and washing were combined, and concentrated under reduced pressure. The concentrated solution was extracted with ethyl acetate. The ethyl acetate solution of the resultant product was dried magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the concentrated residue was purified by silica gel column (hexane→hexane:AcOEt=4:1→2:1→3:2) to give methyl 2-[({2′-[1-(p-methoxybenzyl)-1H-tetrazol-5-yl]biphenyl-4-yl}methyl)amino]-3-aminobenzoate (compound 22a) (1.96 g, 70%) as a brown amorphous solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionto the concentrated residue were added saturated aqueous sodium hydrogen carbonate and ethyl acetate
  5. filtrationfiltered
  6. washthe insoluble material was washed with ethyl acetate
  7. washThe filtrate and washing
  8. concentrationconcentrated under reduced pressure
  9. extractionThe concentrated solution was extracted with ethyl acetate
  10. filtrationfiltered
  11. concentrationThe filtrate was concentrated under reduced pressure
  12. customthe concentrated residue was purified by silica gel column (hexane→hexane:AcOEt=4:1→2:1→3:2)

Sources & evidence

ORD record
ord-e184dd2ad3ff4d5da12024b03d209ca4
Source dataset
uspto-grants-2013_09
Patent number
US08530506B2

Linked notes

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