Water → HCID 59484892, compound

HRID 1408393Notes

Reaction equation

HRID 1408393 reaction equation
C([O-])(=O)C.[O:5]=[C:6]1[N:11]([CH2:12][C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16]([NH2:18])=[NH2+:17])[N:10]=[C:9]([C:22]2[CH:27]=[C:26]([F:28])[C:25]([F:29])=[C:24]([F:30])[CH:23]=2)[CH:8]=[CH:7]1.[CH:31]([CH:33]([CH:39]=O)[C:34]([O:36][CH2:37][CH3:38])=[O:35])=O.O>N1C=CC=CC=1>[O:5]=[C:6]1[N:11]([CH2:12][C:13]2[CH:14]=[C:15]([C:16]3[N:18]=[CH:39][C:33]([C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:31][N:17]=3)[CH:19]=[CH:20][CH:21]=2)[N:10]=[C:9]([C:22]2[CH:23]=[C:24]([F:30])[C:25]([F:29])=[C:26]([F:28])[CH:27]=2)[CH:8]=[CH:7]1

Participants

5

Reactant 3

HCID 962WaterHCID 11029955Ethyl 2-formyl-3-oxopropanoate2×HCID 67223966HCID 67223966, compound

Product 1

HCID 59484892HCID 59484892, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

4.7 g (11.23 mmol) of 3-[6-oxo-3-(3,4,5-trifluorophenyl)-6H-pyridazin-1-ylmethyl]benzamidinium acetate are suspended in 40 ml of pyridine, and 2.4 g (16.85 mmol) of ethyl 2-formyl-3-oxopropionate (prepared in accordance with S. H. Berz et al., Journal of Organic Chemistry 1982, 47, 2216) are added, and the mixture is stirred at 80° C. for 4 h. A further 500 mg (3.47 mmol) of ethyl 2-formyl-3-oxopropionate are subsequently added, and the mixture is stirred at 80° C. for 1 h. The reaction mixture is stirred into 400 ml of water, and the precipitate is filtered off with suction, washed a number of times with water and dried in a drying cabinet. Yield: 4.43 g of “A29” (76%), Rt=3.58 min (method B), ESI 467.

Workup

  1. stirringthe mixture is stirred at 80° C. for 1 h
  2. filtrationthe precipitate is filtered off with suction
  3. washwashed a number of times with water
  4. customdried in a drying cabinet

Sources & evidence

ORD record
ord-2c612867848348e9ba2238165713f131
Source dataset
uspto-grants-2014_12
Patent number
US08921357B2

Reaction notes

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