HCID 58136884, compound → HCID 55279276, compound

HRID 657921Notes

Reaction equation

HRID 657921 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([NH:13][N+:14]([O-])=O)[N:7]=[N:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]>C(O)(=O)C.O.[Zn]>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([NH:13][NH2:14])[N:7]=[N:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

5

Reactant 1

HCID 58136884HCID 58136884, compound

Product 1

HCID 55279276HCID 55279276, compoundYield 50.5%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

N-(5,6-Diethoxypyridazin-3-yl)-N-nitroamine (W4.120; 114 mg) was dissolved in acetic acid (5 ml) and added dropwise while cooling with ice and stirring at between 10 and 20° C. to a mixture of zinc (130 mg) in water (3 ml). Thereafter, the ice bath was removed and the mixture was stirred at RT for 1 h. Then the mixture was alkalized with 10 N sodium hydroxide solution, the aqueous phase was extracted three times with DCM, and the combined DCM phases were dried over sodium sulfate, filtered and concentrated. The residue was purified by means of preparative HPLC (met. A). The clean, product-containing fractions were each combined, freed of the ACN, basified with saturated potassium carbonate solution and then extracted three times with DCM. The combined organic phases were dried over sodium sulfate, filtered and concentrated. 50 mg of the title compound were obtained. LC-MS rt: 0.37 min [M+H]+: 199.2 (met. b)

Workup

  1. additionadded dropwise
  2. temperaturewhile cooling with ice
  3. customThereafter, the ice bath was removed
  4. extractionthe aqueous phase was extracted three times with DCM
  5. dry with materialthe combined DCM phases were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by means of preparative HPLC (
  9. additionThe clean, product-containing fractions
  10. extractionextracted three times with DCM
  11. dry with materialThe combined organic phases were dried over sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-06b50293c4be4caca7037ce57912e503
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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