Acetic Acid → HCID 46873081, compound

HRID 714553Notes

Reaction equation

HRID 714553 reaction equation
C[N:2](C)/[CH:3]=[CH:4]/[C:5]([C:7]1[C:12](=[O:13])[CH:11]=[CH:10][N:9]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[N:8]=1)=O.[Cl:21][C:22]1[N:27]=[C:26]([NH:28]N)[CH:25]=[CH:24][CH:23]=1.C(O)(=O)C>CCO>[Cl:21][C:22]1[N:27]=[C:26]([N:28]2[C:5]([C:7]3[C:12](=[O:13])[CH:11]=[CH:10][N:9]([C:14]4[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=4)[N:8]=3)=[CH:4][CH:3]=[N:2]2)[CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 3200042-Chloro-6-hydrazinopyridineHCID 59436237HCID 59436237, compound

Product 1

HCID 46873081HCID 46873081, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-((E)-3-dimethylamino-acryloyl)-1-pyridin-4-yl-1H-pyridazin-4-one (A-1; 0.075 g; 0.3 mmol) in EtOH (2 ml) was treated with (6-chloropyridin-2-yl)-hydrazine (0.048 g; 0.3 mmol) in a sealed tube and irradiated at 100° C. for 30 min. Acetic acid (0.5 ml) was added and the mixture again irradiated at 100° C. for 15 min. The solvent of the reaction mixture was removed and the crude product purified by preparative HPLC yielding 0.0122 g (12%) of the final product. MS: M=351.1 (M+H)−

Workup

  1. customirradiated at 100° C. for 30 min
  2. customthe mixture again irradiated at 100° C. for 15 min
  3. customThe solvent of the reaction mixture was removed
  4. customthe crude product purified by preparative HPLC

Sources & evidence

ORD record
ord-f9012d422c414bf79b6948d55fb57b9b
Source dataset
uspto-grants-2015_11
Patent number
US09187455B2

Reaction notes

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