1,2-Dichloroethane → N'-Acetyl-4-(Cyclopentylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carbohydrazide

HRID 490874Notes

Reaction equation

HRID 490874 reaction equation
[CH:1]1([NH:6][C:7]2[C:12]([C:13]([OH:15])=O)=[CH:11][N:10]=[C:9]3[N:16]([CH2:19][CH3:20])[N:17]=[CH:18][C:8]=23)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[C:35]([NH:38][NH2:39])(=[O:37])[CH3:36]>CN(C=O)C>[C:35]([NH:38][NH:39][C:13]([C:12]1[C:7]([NH:6][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)=[C:8]2[CH:18]=[N:17][N:16]([CH2:19][CH3:20])[C:9]2=[N:10][CH:11]=1)=[O:15])(=[O:37])[CH3:36]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 14039AcetohydrazideHCID 757711-HydroxybenzotriazoleHCID 576751554-(Cyclopentylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid

Product 1

HCID 57675205N'-Acetyl-4-(Cyclopentylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carbohydrazideYield 54.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Intermediate 3 (0.066 g), EDC (0.06 g) and HOBT (0.035 g) were suspended in DMF (2 ml) and the mixture was stirred for 15 minutes. Acetic hydrazide (0.02 g) was then added and the mixture stirred under nitrogen for 18 h. Solvents were removed by concentration in vacuo and the residue partitioned between DCM and water. The layers were separated and the organic phase was washed with saturated aqueous sodium bicarbonate solution, then concentrated and applied to an SPE cartridge (aminopropyl, 1 g) which was eluted with methanol. Concentration in vacuo afforded Intermediate 4 (0.043 g). LCMS showed MH+=331; TRET=2.38 min.

Workup

  1. stirringthe mixture stirred under nitrogen for 18 h
  2. customSolvents were removed by concentration in vacuo
  3. customthe residue partitioned between DCM and water
  4. customThe layers were separated
  5. washthe organic phase was washed with saturated aqueous sodium bicarbonate solution
  6. concentrationconcentrated
  7. washwas eluted with methanol
  8. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-6918daca97224cb0aa8e8d62b29efc4c
Source dataset
uspto-grants-2009_05
Patent number
US07528148B2

Reaction notes

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