Ammonium formate → HCID 178491270, compound

HRID 631868Notes

Reaction equation

HRID 631868 reaction equation
C([N:8]1[C:12]([C:13]2[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[CH:15][C:14]=2[NH:21][S:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:24])=[O:23])=[N:11][N:10]=[N:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[OH-].[Pd+2].[OH-]>[CH3:20][O:19][C:18]1[C:13]([C:12]2[NH:8][N:9]=[N:10][N:11]=2)=[C:14]([NH:21][S:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:24])=[O:23])[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 68296418HCID 68296418, compound2×

Product 1

HCID 178491270HCID 178491270, compoundYield 61.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of N-[2-(1-benzyl-1H-tetrazol-5-yl)-3-methoxyphenyl]-benzenesulfonamide (Intermediate 12, 0.104 g), ammonium formate (0.45 g) and palladium hydroxide (0.01 g) in ethanol (10 mL) was heated at reflux for 72 hours. The reaction mixture was filtered through celite and the filtrate was evaporated under vacuum. The residue was purified by flash chromatography on silica, eluting with a mixture of DCM and methanol. The fractions containing the desired product were combined and evaporated to give the title compound as a colorless solid (0.05 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 72 hours
  3. filtrationThe reaction mixture was filtered through celite
  4. customthe filtrate was evaporated under vacuum
  5. customThe residue was purified by flash chromatography on silica
  6. washeluting with a mixture of DCM and methanol
  7. additionThe fractions containing the desired product
  8. customevaporated

Sources & evidence

ORD record
ord-ccad89960a8445c1984729ffe298fdba
Source dataset
uspto-grants-2016_04
Patent number
US09321740B2

Reaction notes

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