Acetic Acid → HCID 178526796, compound

HRID 1943917Notes

Reaction equation

HRID 1943917 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[CH:14]=[C:13]([NH2:15])[NH:12][N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[N+:17]([CH:20]([CH:23]=O)[CH:21]=O)([O-:19])=[O:18].[Na].C(O)(=O)C>O>[CH2:1]([O:8][CH2:9][C:10]1[C:14]2[C:13](=[N:15][CH:21]=[C:20]([N+:17]([O-:19])=[O:18])[CH:23]=2)[NH:12][N:11]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 71317419Sodium nitromalonaldehyde hydrateHCID 178507762HCID 178507762, compound

Product 1

HCID 178526796HCID 178526796, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A round-bottom flask was charged with 3-(benzyloxymethyl)-1H-pyrazol-5-amine (1.74 g, 8.56 mmol, Honma, T. et al. “A Novel Approach for the Development of Selective Cdk4 Inhibitors: Library Design Based on Locations of Cdk4 Specific Amino Acid Residues.” J. Med. Chem. Vol. 44, No. 26 (2001): 4628-4640), sodium nitromalonaldehyde monohydrate (1.46 g, 9.42 mmol) and acetic acid (8.7 mL). The reaction mixture was heated at 100° C. for 24 hours. The reaction mixture was poured into water and then extracted with ethyl acetate (2×). The combined organic layers were dried with sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography to afford 3-(benzyloxymethyl)-5-nitro-1H-pyrazolo[3,4-b]pyridine (1.37 g, 56%) as a solid.

Workup

  1. extractionextracted with ethyl acetate (2×)
  2. dry with materialThe combined organic layers were dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-27ecd2a2df3e46f5ad41674bcac6afa8
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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