Hydrazine → HCID 58914780, compound

HRID 1297498Notes

Reaction equation

HRID 1297498 reaction equation
[NH2:1]N.[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[C:11]1[C:12]([N:30]2[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][C:31]2=[O:37])=[C:13](CCCN2C(=O)C3C=CC=CC=3C2=O)[NH:14][CH:15]=1.CCN([CH:44]([CH3:46])[CH3:45])C(C)C.Cl[C:48]1[N:53]=[C:52]([NH2:54])[C:51]([N+:55]([O-:57])=[O:56])=[CH:50][CH:49]=1>CCO>[NH2:54][C:52]1[N:53]=[C:48]([NH:1][CH2:46][CH2:44][CH2:45][N:14]2[CH:15]=[C:11]([C:5]3[CH:6]=[CH:7][C:8]([Cl:10])=[CH:9][C:4]=3[Cl:3])[C:12]([N:30]3[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][C:31]3=[O:37])=[CH:13]2)[CH:49]=[CH:50][C:51]=1[N+:55]([O-:57])=[O:56]

Participants

6

Reactant 4

HCID 9321HydrazineHCID 81531DiisopropylethylamineHCID 27240356-Chloro-3-nitropyridin-2-ylamineHCID 68437854HCID 68437854, compound

Product 1

HCID 58914780HCID 58914780, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Hydrazine (1.3 eq) was added to a solution of 2-{3-[4-(2,4-dichlorophenyl)-3-(4-methyl-2-oxopiperazinyl)pyrrolyl]propyl}benzo[c]azoline-1,3-dione (8) in abs. EtOH and stirred at 75° C. for 2 hours. The reaction developed a white precipitate, which was filtered. The EtOH was concentrated under reduced pressure. The residue was taken up in CH2Cl2 and the precipitate was filtered again. The organic solution was evaporated to a foam. Assuming a quantitative yield, the residue was taken up in CH3CN and DMA (4:1). Hünig's Base (1.3 eq) was added to the mixture followed by 6-chloro-3-nitro-2-pyridylamine (10) (1.2 eq). The reaction was heated to 80° C. for 2 hours until completion was determined by LC/MS. The reaction was subsequently concentrated. The residue was dissolved in EtOAc, washed with water, brine, dried (Na2SO4), filtered, and concentrated to dryness to give 1-(1-{3-[(6-amino-5-nitro(2-pyridyl))amino]propyl}-4-(2,4-dichlorophenyl)pyrrol-3-yl)-4-methylpiperazin-2-one (11). The product (11) was purified by silica column chromatography, eluting with MeOH in CH2Cl2 (5:95, v/v). After collecting the purified fractions and concentrating, light yellow foam (LC/MS m/z 519.4 MH+, 42% yield) was attained in 95% purity.

Workup

  1. filtrationwas filtered
  2. concentrationThe EtOH was concentrated under reduced pressure
  3. filtrationthe precipitate was filtered again
  4. customThe organic solution was evaporated to a foam
  5. concentrationThe reaction was subsequently concentrated
  6. dissolutionThe residue was dissolved in EtOAc
  7. washwashed with water, brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-a62444d0da464a3f98ea0a772131d2cc
Source dataset
uspto-grants-2007_07
Patent number
US07250443B2

Reaction notes

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