Acetic Acid → HCID 57652714, compound

HRID 1013268Notes

Reaction equation

HRID 1013268 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([C:10]2[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:7]=[C:6]([NH2:18])[CH:5]=1.[N-:20]=[N+:21]=[N-:22].[Na+].[CH3:24]C(O)=O>COC(OC)OC>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:5]=[C:6]([N:18]2[CH:24]=[N:22][N:21]=[N:20]2)[CH:7]=[C:8]([C:10]2[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 33557Sodium AzideHCID 57652723HCID 57652723, compound

Product 1

HCID 57652714HCID 57652714, compound

Reagents, catalysts & solvents 1

HCID 9005Trimethyl orthoformateSolvent

Procedure

A suspension of 3-amino-5-(3-methoxy-pyridin-2-yl)-benzoic acid methyl ester (530 mg, 1.96 mmol) in trimethoxymethane (1.5 mL) was stirred under nitrogen for 5 minutes. NaN3 (390 mg, 5.9 mmol) was added slowly, followed by HOAc (10 mL). The reaction mixture was stirred at room temperature for 72 hours, then was concentrated under reduced pressure. The residue was partitioned between water and EtOAc. The combined organic layers were washed with water, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified via flash chromatography through 80 g of silica using EtOAc/hexanes (20%-100%) to give 170 mg of 3-(3-methoxy-pyridin-2-yl)-5-tetrazol-1-yl-benzoic acid methyl ester, MS (M+H)=312.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 72 hours
  2. concentrationwas concentrated under reduced pressure
  3. customThe residue was partitioned between water and EtOAc
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified via flash chromatography through 80 g of silica

Sources & evidence

ORD record
ord-922f6d0bcf124c58be931291d069cad2
Source dataset
uspto-grants-2011_07
Patent number
US07981914B2

Reaction notes

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