Hydrochloric Acid → HCID 24957398, compound

HRID 1894186Notes

Reaction equation

HRID 1894186 reaction equation
C(OC([C:6]1[O:7][C:8]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[N:22]4[CH:23]=[CH:24][C:25]([C:27]5[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=5)=[CH:26][C:21]4=[N:20][CH:19]=3)[CH:13]=2)=[N:9][N:10]=1)=O)C.[OH-].[Na+].Cl>O1CCOCC1.CCOCC>[F:33][C:30]1[CH:29]=[CH:28][C:27]([C:25]2[CH:24]=[CH:23][N:22]3[C:18]([C:14]4[CH:13]=[C:12]([NH:11][C:8]5[O:7][CH:6]=[N:10][N:9]=5)[CH:17]=[CH:16][CH:15]=4)=[CH:19][N:20]=[C:21]3[CH:26]=2)=[CH:32][CH:31]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59277774HCID 59277774, compound

Product 1

HCID 24957398HCID 24957398, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

5-{3-[7-(4-Fluoro-phenyl)-imidazo[1,2-a]pyridin-3-yl]-phenylamino}-[1,3,4]oxadiazole-2-carboxylic acid ethyl ester (120 mg, 0.27 mmol) and 5N NaOH (0.5 ml, 2.5 mmol) in dioxane (2 ml) was stirred and heated at 100° C. for 1 hour. After cooling to RT, 5N HCl (0.5 ml) was added. The mixture was diluted with Et2O and the liquid was decanted off. The residue was treated with EtOH and the solid was collected by filtration. This solid was suspended in EtOH (3 ml) and heated at reflux for 15 minutes. The volatiles were removed in vacuo and the residue was purified by preparative HPLC to give the title compound (12 mg).

Workup

  1. temperatureAfter cooling to RT
  2. customthe liquid was decanted off
  3. additionThe residue was treated with EtOH
  4. filtrationthe solid was collected by filtration
  5. temperatureheated
  6. temperatureat reflux for 15 minutes
  7. customThe volatiles were removed in vacuo
  8. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-115e20251cbc49d0aed454565d6091e6
Source dataset
uspto-grants-2013_08
Patent number
US08513276B2

Reaction notes

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