Acetic Acid → HCID 67088839, compound

HRID 1943900Notes

Reaction equation

HRID 1943900 reaction equation
[CH:1](=O)[CH3:2].[C:4](O)(=O)[CH3:5].[N+:8]([C:11]1[CH:12]=[C:13]2[C:19]([NH2:20])=[N:18][NH:17][C:14]2=[N:15][CH:16]=1)([O-:10])=[O:9].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C1COCC1.ClC(Cl)C.C(OCC)(=O)C>[CH2:4]([N:20]([CH2:1][CH3:2])[C:19]1[C:13]2[C:14](=[N:15][CH:16]=[C:11]([N+:8]([O-:10])=[O:9])[CH:12]=2)[NH:17][N:18]=1)[CH3:5]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 178509234HCID 178509234, compound

Product 1

HCID 67088839HCID 67088839, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21943919HCID 21943919, compoundSolvent

Procedure

Acetaldehyde (0.258 g, 5.86 mmol) and a drop of acetic acid were added to a solution of 5-nitro-1H-pyrazolo[3,4-b]pyridin-3-amine (0.105 g, 0.586 mmol) in THF/dichloroethane (“DCE”) (12 mL, 1:1). NaBH(OAc)3 (1.24 g, 5.86 mmol) was added, and the mixture was left at room temperature for 60 hours. The reaction mixture was diluted with ethyl acetate (50 mL) and quenched with water (10 mL). The aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organic layers were dried, filtered and concentrated. The crude product was purified by column chromatography, eluting with hexanes/ethyl acetate (9:1), hexanes/ethyl acetate (4:1) to give N,N-diethyl-5-nitro-1H-pyrazolo[3,4-b]pyridin-3-amine (22 mg, 16% yield) as a solid.

Workup

  1. customquenched with water (10 mL)
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×50 mL)
  3. customThe combined organic layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography
  7. washeluting with hexanes/ethyl acetate (9:1), hexanes/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-59d45b8d87164ee9805d83e832e37e73
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

Loading…