(2,5-difluorophenyl)hydrazine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Add 1,1,3,3-tetramethoxypropane (8.2 g, 50 mmol) to a mixture of 2,5-difluorophenylhydrazine (9.022 g, 62.6 mmol) and hydrochloric acid (5M, 5 mL, 25 mmol) in ethanol (50 mL) and heat and stir under reflux under nitrogen for 17 hr. Cool the mixture, evaporate the ethanol in vacuo, suspend the residue in DCM (80 mL), filter the DCM solution and pass through an SCX-2 column. Collect the eluent and pass through a second SCX2 column and evaporate the eluent to give 1-(2,5-difluoro-phenyl)-1H-pyrazol as a liquid (8.79 g, 97%). MS (m/z): 181 (M+1). heat under reflux under nitrogen for 17 hr Cool the mixture evaporate the ethanol in vacuo filter the DCM solution and pass through an SCX-2 column Collect the eluent evaporate the eluent

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The product was obtained starting from 3-((E)-3-Dimethylamino-acryloyl)-1-[3-(pyrrolidine-1-sulfonyl)-phenyl]-1H-pyridazin-4-one (A-29) and 2,5-difluoro-phenylhydrazine according to the method described for example 91. MS: M=484.1 (M+H)+ The product was obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The product was obtained starting from 3-[3-((E)-3-Dimethylamino-acryloyl)-4-oxo-4H-pyridazin-1-yl]-benzonitrile (A-19) and 2,5-difluoro-phenylhydrazine according to the method described for example 91. MS: M=376.2 (M+H)+ The product was obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The product was obtained starting from 3-[3-((E)-3-Dimethylamino-acryloyl)-4-oxo-4H-pyridazin-1-yl]-N,N-dimethyl-benzenesulfonamide (A-12) and 2,5-difluoro-phenylhydrazine according to the method described for example 91. MS: M=458.2 (M+H)+ The product was obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The product was obtained starting from 1-(2,2-Difluoro-benzo[1,3]dioxol-5-yl)-3-((E)-3-dimethylamino-acryloyl)-1H-pyridazin-4-one (A-11) and 2,5-difluoro-phenylhydrazine according to the method described for example 91. MS: M=431.2 (M+H)+ The product was obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The product was obtained starting from 1-(3-Difluoromethoxy-phenyl)-3-((E)-3-dimethylamino-acryloyl)-1H-pyridazin-4-one (A-10) and 2,5-difluoro-phenylhydrazine according to the method described for example 91. MS: M=417.2 (M+H)+ The product was obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Reaction of 3-((E)-3-dimethylamino-acryloyl)-1-(3-methansulfonyl-phenyl)-1H-pyridazin-4-one (A-7) and (2,5-difluoro-phenyl)-hydrazine according to example 43 gave the desired product. MS: M=428.6 (M+H)+

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The product was obtained starting from 3-((E)-3-Dimethylamino-acryloyl)-1-(3-trifluoromethyl-phenyl)-1H-pyridazin-4-one (A-3) and 2,5-difluorophenylhydrazine according to the method described for Example 1 in 32% yield. MS: M=419.1 (M+H)+ The product was obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The product was obtained starting from 3-((E)-3-Dimethylamino-acryloyl)-1-(4-trifluoromethoxy-phenyl)-1H-pyridazin-4-one (A-8) and 2,5-difluoro-phenylhydrazine according to the method described for example 91. MS: M=435.3 (M+H)+ The product was obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The product was obtained starting from 1-(2,2-Difluoro-benzo[1,3]dioxol-4-yl)-3-((E)-3-dimethylamino-acryloyl)-1H-pyridazin-4-one (A-15) and 2,5-difluoro-phenylhydrazine according to the method described for example 91. MS: M=431.2 (M+H)+ The product was obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Reaction of 3-((E)-3-dimethylamino-acryloyl)-1-(3-trifluoromethoxy-phenyl)-1H-pyridazin-4-one (A-6) and (2,5-difluoro-phenyl)-hydrazine according to example 43 gave the desired product. MS: M=435.0 (M+H)+

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The product was obtained starting from 3-((E)-3-Dimethylamino-acryloyl)-1-phenyl-1H-pyridazin-4-one (A-1) and 2,5-difluorophenylhydrazine according to the method described for Example 1 in 24% yield. MS: M=351.1 (M+H)+ The product was obtained