Pyridine → N-(2-(3-(4-Cyano-3-nitrophenyl)-1H-pyrazol-1-yl)ethyl)-3-(1-(hydroxyimino)ethyl)-1H-pyrazole-5-carboxamide

HRID 872553Notes

Reaction equation

HRID 872553 reaction equation
[C:1]([C:4]1[NH:8][N:7]=[C:6]([C:9]([NH:11][CH2:12][CH2:13][N:14]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[C:21]([N+:27]([O-:29])=[O:28])[CH:20]=3)=[N:15]2)=[O:10])[CH:5]=1)(=O)[CH3:2].C([O-])(=O)C.[Na+].Cl.[NH2:36][OH:37].N1C=CC=CC=1>C(O)C>[C:25]([C:22]1[CH:23]=[CH:24][C:19]([C:16]2[CH:17]=[CH:18][N:14]([CH2:13][CH2:12][NH:11][C:9]([C:6]3[NH:7][N:8]=[C:4]([C:1](=[N:36][OH:37])[CH3:2])[CH:5]=3)=[O:10])[N:15]=2)=[CH:20][C:21]=1[N+:27]([O-:29])=[O:28])#[N:26]

Participants

6

Reactant 4

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 178466819HCID 178466819, compound

Product 1

HCID 136350314N-(2-(3-(4-Cyano-3-nitrophenyl)-1H-pyrazol-1-yl)ethyl)-3-(1-(hydroxyimino)ethyl)-1H-pyrazole-5-carboxamideYield 19.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Acetyl-N-(2-(3-(4-cyano-3-nitrophenyl)-1H-pyrazol-1-yl)ethyl)-1H-pyrazole-3-carboxamide (0.17 g, 0.43 mmol) was dissolved in ethanol (15 ml). Sodium acetate (0.071 g, 0.86 mmol) and hydroxylamine hydrochloride (0.060 g, 0.86 mmol) was added and the reaction mixture was stirred at RT for 1.5 h. After addition of pyridine (5 ml) stirring was continued for 65 h. The reaction mixture was evaporated to dryness, co-evaporated two times with toluene and dissolved the residue in ethyl acetate. It was then washed two times with water, dried with Na2SO4 and purified with CombiFlash using DCM and methanol as eluents affording 0.034 g of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 2.11-2.15 (m, 3H), 3.68-3.71 (m, 2H), 4.39 (t, 2H), 7.05-7.06 (m, 1H), 7.88 (d, 1H), 8.17-8.20 (m, 1H), 8.32-8-35 (m, 1H), 8.68 (d, 1H).

Workup

  1. stirringstirring
  2. waitwas continued for 65 h
  3. customThe reaction mixture was evaporated to dryness
  4. dissolutiondissolved the residue in ethyl acetate
  5. washIt was then washed two times with water
  6. dry with materialdried with Na2SO4
  7. custompurified with CombiFlash

Sources & evidence

ORD record
ord-33b466709c0e49479f2355ef7a7c73d3
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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