Sodium Bicarbonate → HCID 178517780, compound

HRID 1867884Notes

Reaction equation

HRID 1867884 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)=[CH:10][C:11]2[N:12]([C:14]([CH2:17][C:18]3[C:19]([O:28]C)=[N:20][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:23]=3)=[N:15][N:16]=2)[N:13]=1.C([O-])(O)=O.[Na+]>Br>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([C:30]2[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=2)=[CH:10][C:11]2[N:12]([C:14]([CH2:17][C:18]3[C:19]([OH:28])=[N:20][C:21]([C:24]([F:26])([F:25])[F:27])=[CH:22][CH:23]=3)=[N:15][N:16]=2)[N:13]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 11993398HCID 11993398, compound

Product 1

HCID 178517780HCID 178517780, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A suspension of 6-(2-chlorophenyl)-7-(4-chlorophenyl)-3-((2-methoxy-6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazine (Example 26) (100 mg, 0.19 mmol) in aqueous (48%) hydrobromic acid (2 mL) was refluxed for 1 h. After cooling to room temperature, the reaction mixture was adjusted to pH 7-8 by careful addition of saturated aqueous NaHCO3. The resulting suspension was filtered, and the collected solid was washed with water (10 mL×2), diethyl ether (5 mL), dried in a 50° C. vacuum oven overnight to afford 60 mg (62%) of the title compound as an off-white solid. HPLC/MS (method A): retention time=3.53 min, (M+H)+=516.0.

Workup

  1. temperaturewas refluxed for 1 h
  2. filtrationThe resulting suspension was filtered
  3. washthe collected solid was washed with water (10 mL×2), diethyl ether (5 mL)
  4. customdried in a 50° C. vacuum oven overnight

Sources & evidence

ORD record
ord-f204c37a9b784b57ae7b7666237d9659
Source dataset
uspto-grants-2009_12
Patent number
US07632837B2

Reaction notes

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