Hydrochloric Acid → HCID 178515849, compound

HRID 1792599Notes

Reaction equation

HRID 1792599 reaction equation
C[O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[C:19]([C:20]4[CH:21]=[CH:22][C:23]5[N:24]([C:26]([C:29]6[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=6)=[CH:27][N:28]=5)[CH:25]=4)=[CH:18][N:17](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:16]=3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.Cl.[OH-].[Na+]>C(O)C>[N:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[C:26]1[N:24]2[CH:25]=[C:20]([C:19]3[C:15]([C:12]4[CH:11]=[CH:10][C:9]([C:6]5[CH:5]=[CH:4][C:3](=[O:2])[NH:8][CH:7]=5)=[CH:14][CH:13]=4)=[N:16][NH:17][CH:18]=3)[CH:21]=[CH:22][C:23]2=[N:28][CH:27]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22031832HCID 22031832, compound

Product 1

HCID 178515849HCID 178515849, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 114 mg 6-{3-[4-(6-methoxypyridin-3-yl)phenyl]-1-trityl-1H-pyrazol-4-yl}-3-(pyridin-2-yl)imidazo[1,2-a]pyridine (compound in Example 365), 4 mL of 5 N hydrochloric acid and 4 mL ethanol was heated overnight under reflux. The reaction solution was basified with 5 N sodium hydroxide under ice-coolingd water, and the precipitated crystals were collected by filtration. The crystals were dried over hot air at 70° C., then dissolved in a mixture of methanol and dichloromethane and filtered. The filtrate was evaporated, then ethyl acetate was added to the residue which was then triturated, and the crystals were collected by filtration and dried under reduced pressure with a vacuum pump, to give 36 mg of the title compound as white crystals.

Workup

  1. temperaturewas heated overnight
  2. temperatureunder reflux
  3. filtrationthe precipitated crystals were collected by filtration
  4. customThe crystals were dried over hot air at 70° C.
  5. dissolutiondissolved in a mixture of methanol and dichloromethane
  6. filtrationfiltered
  7. customThe filtrate was evaporated
  8. additionethyl acetate was added to the residue which
  9. customwas then triturated
  10. filtrationthe crystals were collected by filtration
  11. customdried under reduced pressure with a vacuum pump

Sources & evidence

ORD record
ord-4203c575fb7b436d8fee44ca9b1054de
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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