Water → HCID 22169694, compound

HRID 1822681Notes

Reaction equation

HRID 1822681 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)=[CH:12][N:11]=[N:10][C:9]=2[NH:21][NH2:22])=[CH:4][CH:3]=1.[OH2:23]>CC(O)=O>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]2[CH:12]=[N:11][N:10]3[C:2](=[O:23])[C:3]([CH2:4][CH:5]([CH3:8])[CH3:6])=[N:22][N:21]=[C:9]3[C:8]=2[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 962WaterHCID 22169696HCID 22169696, compound

Product 1

HCID 22169694HCID 22169694, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 1-(4,5-bis(4-chlorophenyl)pyridazin-3-yl)hydrazine (50.0 mg, 0.15 mmol) in AcOH (1 mL) was added (CH3)2CH2COCO2H (40.0 mg, 0.3 mmol). The solution was stirred at RT for 30 min then was heated at 120° C. for 5 h. The reaction mixture was cooled to RT and then poured into water (20 mL). The resultant solution was extracted with EtOAc (20 mL). The organic laer was dried over Na2SO4, filered and concentrate to give the a brown solid. The solid was purified by reverse phase preparative HPLC to give the title compound 9-bis-(4-chloro-phenyl)-3-isobutyl-pyridazino[6,1-c][1,2,4]triazin-4-one, (23.0 mg, 0.054 mmol) as a solid. HPLC retention time=3.87 min; MS observed=425 (M+H); 1H NMR (CDCl3, 500 MHz) δ 8.72 (s, 1H), 7.37–7.33 (m, 4H), 7.24 (d, J=8.8 Hz, 2H), 7.11 (d, J=8.8 Hz, 2H), 2.96 (d, J=7.1 Hz, 2H), 2.34 (m, 1H), 0.99 (d, J=9.3 Hz, 6H).

Workup

  1. temperaturethen was heated at 120° C. for 5 h
  2. temperatureThe reaction mixture was cooled to RT
  3. extractionThe resultant solution was extracted with EtOAc (20 mL)
  4. dry with materialThe organic laer was dried over Na2SO4
  5. concentrationconcentrate
  6. customto give the a brown solid
  7. customThe solid was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-b5412d2942ed432199bfb200e7456379
Source dataset
uspto-grants-2006_05
Patent number
US07037910B2

Reaction notes

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