Acetic Acid → HCID 59716656, compound

HRID 2224225Notes

Reaction equation

HRID 2224225 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][N:12]1[C:34](=[O:35])[N:15]2[N:16]=[CH:17][C:18]([C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)=[C:19]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)[C:14]2=[N:13]1)(=O)C.O(C)[Na].C(O)(=O)C>CO>[OH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][N:12]1[C:34](=[O:35])[N:15]2[N:16]=[CH:17][C:18]([C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)=[C:19]([C:20]3[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=3)[C:14]2=[N:13]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 59716641HCID 59716641, compound2×HCID 178418582HCID 178418582, compound

Product 1

HCID 59716656HCID 59716656, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2-((7,8-Bis(4-chlorophenyl)-3-oxo-[1,2,4]triazolo[4,3-b]pyridazin-2(3H)-yl)methyl)phenyl acetate, prepared as described in 25A, (1.13 g), was dissolved in 25 mL of CH3OH. A solution of NaOCH3 (121 mg, 2.24 mmol) in a small amount of CH3OH (2 mL) was added to the reaction, and then, the reaction was stirred overnight. After this time, 0.3 mL of acetic acid was added to the reaction. The reaction was stirred for an additional 10 min, and then the resultant solution was concentrated under reduced pressure. The crude residue was purified using silica gel column chromatography using an automated system, eluting with a gradient of 0% to 60% EtOAc/hexanes for 30 min followed by 60% EtOAc/hexanes for an additional 15 min. The title compound, 2-(2-hydroxybenzyl)-7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (818 mg, 79% yield) was obtained as yellow solid. MS [M+H]+=463; 1H NMR (CDCl3, 400 MHz) δ 8.54 (s, 1H), 8.14 (s, 1H), 7.32-7.17 (m, 8H), 7.04-7.00 (m, 2H), 6.94 (dd, 1H), 6.81 (td, 1H), 5.13 (s, 2H).

Workup

  1. stirringThe reaction was stirred for an additional 10 min
  2. concentrationthe resultant solution was concentrated under reduced pressure
  3. customThe crude residue was purified
  4. washeluting with a gradient of 0% to 60% EtOAc/hexanes for 30 min
  5. waitfollowed by 60% EtOAc/hexanes for an additional 15 min

Sources & evidence

ORD record
ord-d9139a734ea944ada14ef0b19cb37de8
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

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