Methanol → HCID 178488737, compound

HRID 1792600Notes

Reaction equation

HRID 1792600 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]3[CH:14]=[C:15]([C:18]4[C:19]([C:42]5[CH:47]=[CH:46][C:45]([C:48]6[C:49]([C:54]([O:56]C)=[O:55])=[CH:50][CH:51]=[CH:52][CH:53]=6)=[CH:44][CH:43]=5)=[N:20][N:21](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[CH:22]=4)[CH:16]=[CH:17][C:12]3=[N:11][CH:10]=2)=[CH:5][CH:4]=1.[OH-].[Na+].CO.[Cl-].[NH4+]>O.O1CCCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]3[CH:14]=[C:15]([C:18]4[C:19]([C:42]5[CH:47]=[CH:46][C:45]([C:48]6[C:49]([C:54]([OH:56])=[O:55])=[CH:50][CH:51]=[CH:52][CH:53]=6)=[CH:44][CH:43]=5)=[N:20][NH:21][CH:22]=4)[CH:16]=[CH:17][C:12]3=[N:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 22031598HCID 22031598, compound

Product 1

HCID 178488737HCID 178488737, compoundYield 38.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 119 mg methyl 4′-{4-[3-(4-methoxyphenyl)-imidazo[1,2-a]pyridin-6-yl]-1-trityl-1H-pyrazol-3-yl}biphenyl-2-carboxylate (compound in Example 387), 0.5 mL of 1 N aqueous sodium hydroxide and 3 mL methanol was heated at 60° C. overnight under reflux. An aqueous saturated ammonium chloride solution, ethyl acetate, tetrahydrofuran and water were added to the reaction solution, and the organic layer was separated, washed with brine and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was evaporated. 134 mg crude product of 4′-{4-[3-(4-methoxyphenyl)imidazo[1,2-a]pyridin-6-yl]-1-trityl-1H-pyrazol-3-yl}biphenyl-2-carboxylic acid was obtained as a colorless amorphous. From this compound, 30 mg of the title compound was obtained as white crystals by the same method as in Example 84.

Workup

  1. temperatureunder reflux
  2. customthe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe drying agent was filtered off
  6. customthe filtrate was evaporated
  7. custom134 mg crude product of 4′-{4-[3-(4-methoxyphenyl)imidazo[1,2-a]pyridin-6-yl]-1-trityl-1H-pyrazol-3-yl}biphenyl-2-carboxylic acid was obtained as a colorless amorphous

Sources & evidence

ORD record
ord-e0b89ebd62ce41e693afae7533a5ade6
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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