Methanol → 2-Propyl-3-[[2′-(2H-tetrazol-5-yl)[1,1′-biphenyl]-4-yl]oxy]-4-quinolinecarboxylic acid

HRID 1953849Notes

Reaction equation

HRID 1953849 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]([O:15][C:16]2[C:17]([CH2:29][CH2:30][CH3:31])=[N:18][C:19]3[C:24]([C:25]=2[C:26]([OH:28])=[O:27])=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:11][CH:10]=1)#[N:2].C([Sn]([N:45]=[N+:46]=[N-:47])(CCCC)CCCC)CCC.CO>CC1C=CC=CC=1C>[CH2:29]([C:17]1[C:16]([O: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[N:45]=[N:46][NH:47][N:2]=3)=[CH:14][CH:13]=2)=[C:25]([C:26]([OH:28])=[O:27])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=1)[CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 887MethanolHCID 4984872Tributyltin azideHCID 15480212HCID 15480212, compound

Product 1

HCID 98044232-Propyl-3-[[2′-(2H-tetrazol-5-yl)[1,1′-biphenyl]-4-yl]oxy]-4-quinolinecarboxylic acidYield 253.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of the title E compound of Example 1, 3-[(2'-cyano[1,1'-biphenyl]-4-yl)oxy]-2-propyl-4-quinolinecarboxylic acid (3.9 g, 9.6 mmol) and tri-n-butyltin azide (9.6 g, 28.9 mmol) in o-xylene (3.9 mL) was heated to 108° C. for 48 hours. After cooling to room temperature, methanol (15 mL) was added and the dark brown solution was stirred for 20 minutes. The methanol was removed under vacuum, more methanol was added (15 mL), the reaction mixture was stirred briefly and concentrated again. The residue was dissolved in ethyl acetate (500 mL), washed three times with 1.0M trisodium citrate solution, brine, dried over sodium sulfate, and concentrated to yield a brown, viscous oil (10.98 g). Flash chromatography on silica gel (659 g), eluting with 70:25:5 toluene:acetone:acetic acid yielded the title compound as a light yellow solid 2.14 g).

Workup

  1. customThe methanol was removed under vacuum, more methanol
  2. additionwas added (15 mL)
  3. stirringthe reaction mixture was stirred briefly
  4. concentrationconcentrated again
  5. dissolutionThe residue was dissolved in ethyl acetate (500 mL)
  6. washwashed three times with 1.0M trisodium citrate solution, brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-fced192c80064c19b8bae7df26c27429
Source dataset
uspto-grants-2000_09
Patent number
US06117885

Reaction notes

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