Hydrazine hydrate (1:1) → HCID 59716704, compound

HRID 2224220Notes

Reaction equation

HRID 2224220 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:30])[N:15]([CH2:17][CH2:18][N:19]4C(=O)C5C(=CC=CC=5)C4=O)[N:16]=[C:10]3[C:9]=2[C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=2)=[CH:4][CH:3]=1.O.NN>C(O)C.C(OCC)(=O)C>[NH2:19][CH2:18][CH2:17][N:15]1[C:14](=[O:30])[N:11]2[N:12]=[CH:13][C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)=[C:9]([C:31]3[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=3)[C:10]2=[N:16]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59716899HCID 59716899, compound

Product 1

HCID 59716704HCID 59716704, compoundYield 16.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(2-(7,8-Bis(4-chlorophenyl)-3-oxo-[1,2,4]triazolo[4,3-b]pyridazin-2(3H)-yl)ethyl)isoindoline-1,3-dione (180 mg, 0.34 mmol) was reacted with hyrazine hydrate (0.9 ml, 18.5 mmol) in ethanol (10 ml) and stirred overnight. After this time, the reaction mixture was diluted with ethyl acetate and washed with saturated aqueous NaCl. The organic layer was dried over Na2SO4, filtered and concentrated. The crude material was purified by preparative HPLC to give the title compound, 2-(2-aminoethyl)-7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (22 mg, 13%) as a yellow foam. MS M+H=400; 1H NMR (CDCl3) δ 8.12 (broad, 2H), 7.38-7.15 (6H), 7.05 (2H), 4.45 (2H), 3.59 (2H).

Workup

  1. washwashed with saturated aqueous NaCl
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified by preparative HPLC

Sources & evidence

ORD record
ord-3d11b875d17f47a58642ccc6a7e6f2b8
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

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