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

HRID 490877

Reaction equation

HRID 490877 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:40][NH2:41])(=[O:39])[CH:36]([CH3:38])[CH3:37]>CN(C=O)C>[CH:1]1([NH:6][C:7]2[C:12]([C:13]([NH:41][NH:40][C:35](=[O:39])[CH:36]([CH3:38])[CH3:37])=[O:15])=[CH:11][N:10]=[C:9]3[N:16]([CH2:19][CH3:20])[N:17]=[CH:18][C:8]=23)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 192392-MethylpropanehydrazideHCID 757711-HydroxybenzotriazoleHCID 576751554-(Cyclopentylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid

Product 1

HCID 576751924-(Cyclopentylamino)-1-ethyl-N'-isobutyryl-1H-pyrazolo[3,4-b]pyridine-5-carbohydrazide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Intermediate 3 (0.060 g), EDC (0.06 g) and HOBT (0.035 g) were suspended in DMF (2 ml) and stirred under nitrogen for 15 minutes. Isobutyric acid hydrazide (0.027 g) was then added and the mixture stirred under nitrogen for 18 h. Solvents were removed in vacuo and the residue partitioned between DCM and water. The organic phase was washed with saturated aqueous sodium bicarbonate solution, then concentrated in vacuo and applied to an SPE cartridge (aminopropyl, 1 g) which was eluted with methanol. Concentration in vacuo afforded Intermediate 10. LCMS showed MH+=359; TRET=2.70 min.

Workup

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

Sources & evidence

ORD record
ord-4a9655ea6f8640b3bb2a4d9c0eecd8dc
Source dataset
uspto-grants-2009_05
Patent number
US07528148B2

Linked notes

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