Potassium Carbonate → 2-Cyclopropyl-3-[[2'-[2-(triphenylmethyl)-2H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]oxy]-4-quinolinecarboxylic acid, (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl ester

HRID 1953841Notes

Reaction equation

HRID 1953841 reaction equation
[CH:1]1([C:4]2C(OC3C=CC(C4C=CC=CC=4C4N=NN(C(OC(=O)C(C)(C)C)C(C)C)N=4)=CC=3)=C(C(O)=O)C3C(=CC=CC=3)N=2)[CH2:3][CH2:2]1.[CH:46]1([C:49]2[C:58]([O:59][C:60]3[CH:65]=[CH:64][C:63]([C:66]4[CH:71]=[CH:70][CH:69]=[CH:68][C:67]=4[C:72]4[N:73]=[N:74][N:75]([C:77]([C:90]5[CH:95]=[CH:94][CH:93]=[CH:92][CH:91]=5)([C:84]5[CH:89]=[CH:88][CH:87]=[CH:86][CH:85]=5)[C:78]5[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=5)[N:76]=4)=[CH:62][CH:61]=3)=[C:57]([C:96]([OH:98])=[O:97])[C:56]3[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=3)[N:50]=2)[CH2:48][CH2:47]1.[C:99](=[O:102])([O-:101])[O-:100].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[CH:46]1([C:49]2[C:58]([O:59][C:60]3[CH:61]=[CH:62][C:63]([C:66]4[CH:71]=[CH:70][CH:69]=[CH:68][C:67]=4[C:72]4[N:73]=[N:74][N:75]([C:77]([C:90]5[CH:91]=[CH:92][CH:93]=[CH:94][CH:95]=5)([C:78]5[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=5)[C:84]5[CH:85]=[CH:86][CH:87]=[CH:88][CH:89]=5)[N:76]=4)=[CH:64][CH:65]=3)=[C:57]([C:96]([O:98][CH2:4][C:1]3[O:102][C:99](=[O:101])[O:100][C:2]=3[CH3:3])=[O:97])[C:56]3[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=3)[N:50]=2)[CH2:47][CH2:48]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 100774042-Cyclopropyl-3-[[2'-[2-[1-(2,2-dimethyl-1-oxopropoxy)-2-methylpropyl]-2H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]oxy]-4-quinolinecarboxylic acidHCID 23298234HCID 23298234, compound

Product 1

HCID 571027302-Cyclopropyl-3-[[2'-[2-(triphenylmethyl)-2H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]oxy]-4-quinolinecarboxylic acid, (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the title A compound of Example 17, 2-cyclopropyl-3-[[2'-[2-(triphenylmethyl)-2H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]oxy]-4-quinolinecarboxylic acid (1.32 g, 1.91 mmol, 1 eq.), and the title B compound (1.84 g, 9.54 mmol, 5 eq.) in dimethylformamide (3.8 mL, 0.5M), potassium carbonate (0.66 g, 4.77 mmol, 2.5 eq.) was added. The mixture was stirred at room temperature for 21 hours, diluted with ethyl acetate and filtered. The filtrate was washed with ammonium chloride/water and saturated sodium chloride, dried (magnesium sulfate), filtered and concentrated to afford the title compound.

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with ammonium chloride/water and saturated sodium chloride
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8425e42db29e42a490c7e9a96d46d5bc
Source dataset
uspto-grants-2000_09
Patent number
US06117885

Reaction notes

Loading…