Dimethylformamide → HCID 59716501, compound

HRID 2224221Notes

Reaction equation

HRID 2224221 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[N:12][N:11]3[C:14](=O)[NH:15][N:16]=[C:10]3[C:9]=2[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.[C:25]([O-:28])([O-])=O.[K+].[K+].CN([CH:34]=[O:35])C>C(OCC)(=O)C.Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[N:12][N:11]3[C:25](=[O:28])[N:15]([CH2:14][C@@H:34]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=4)[OH:35])[N:16]=[C:10]3[C:9]=2[C:18]2[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 111641617,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one

Product 1

HCID 59716501HCID 59716501, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, (20 mg, 0.06 mmol) prepared as described in Example 1, in 0.25 mL of DMF was added R-(+)-3-chlorostyrene oxide (0.007 mL, 0.06 mmol) and 15 mg of K2CO3. The resulting red solution was heated to 60° C. for 19 h and, upon cooling to RT, the mixture was diluted with 5 mL of ethyl acetate and 5 mL of 1N HCl. The layers were separated, and the organic layer was washed with 5 mL of saturated aqueous NaCl. The organic layer was dried over MgSO4, filtered and evaporated to give a yellow oil. The material was purified using reverse-phase HPLC to give the title compound, (R)-7,8-bis(4-chlorophenyl)-2-(2-(3-chlorophenyl)-2-hydroxyethyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, (15 mg, 52% yield) as a yellow solid. HRMS Anal. Calc'd for C25H17Cl3N4O2, 510.04, [M+H]+=511.0509 observed. 1H NMR (400 MHz, CDCl3) δ 8.01 (s, 1H), 7.16 (s, 1H), 7.15-7.05 (m, 9H), 6.92 (d, 2H, J=8.6 Hz), 5.05-4.95 (m, 1H), 4.13-4.08 (m, 2H), 1.55 (br s, 1H).

Workup

  1. temperatureupon cooling to RT
  2. customThe layers were separated
  3. washthe organic layer was washed with 5 mL of saturated aqueous NaCl
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give a yellow oil
  8. customThe material was purified

Sources & evidence

ORD record
ord-14eda393c24f46759bccbcd2f6d2e249
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

Loading…