Hydrogen Bromide → HCID 178515974, compound

HRID 1792533Notes

Reaction equation

HRID 1792533 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:14]=[CH:15][C:16]4[N:17]([C:19]([C:22]5[CH:27]=[CH:26][CH:25]=[C:24]([O:28]C)[N:23]=5)=[CH:20][N:21]=4)[CH:18]=3)=[CH:11][N:10](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:9]=2)=[CH:4][CH:3]=1.Br.[OH-].[Na+]>C(O)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([C:13]3[CH:14]=[CH:15][C:16]4[N:17]([C:19]([C:22]5[NH:23][C:24](=[O:28])[CH:25]=[CH:26][CH:27]=5)=[CH:20][N:21]=4)[CH:18]=3)=[CH:11][NH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 22031149HCID 22031149, compound

Product 1

HCID 178515974HCID 178515974, compoundYield 16.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 54 mg 6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]-3-(6-methoxy-2-pyridyl)imidazo[1,2-a]pyridine obtained in Example 23, 2 mL of 48% hydrobromic acid and 2 mL acetic acid was stirred at room temperature for 4 hours and then heated for 10 minutes under reflux. The reaction solution was cooled and neutralized with 5 N aqueous sodium hydroxide, and the precipitated solid was collected by filtration, washed with water and air-dried. Then, the solid was triturated with diethyl ether, collected by filtration and dried in vacuo to give 5.4 mg of the title compound as white crystals.

Workup

  1. temperatureheated for 10 minutes
  2. temperatureunder reflux
  3. temperatureThe reaction solution was cooled
  4. filtrationthe precipitated solid was collected by filtration
  5. washwashed with water
  6. customair-dried
  7. customThen, the solid was triturated with diethyl ether
  8. filtrationcollected by filtration
  9. customdried in vacuo

Sources & evidence

ORD record
ord-5164d061d2834a26818985e1695dbc41
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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