Cyclopentylamine → HCID 18446602, compound

HRID 1269031Notes

Reaction equation

HRID 1269031 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[C:10]([C:11](=[O:13])[CH3:12])=[C:6]2[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH:26]1([NH2:31])[CH2:30][CH2:29][CH2:28][CH2:27]1.C(OCC)(=O)C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH:26]1([NH:31][C:2]2[N:7]3[N:8]=[C:9]([C:14]4[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=4)[C:10]([C:11](=[O:13])[CH3:12])=[C:6]3[CH:5]=[CH:4][CH:3]=2)[CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

9

Reactant 4

HCID 2906CyclopentylamineHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 18446599HCID 18446599, compound

Product 1

HCID 18446602HCID 18446602, compoundYield 80%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 634876Binap, (A+-)-CatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-[7-chloro-2-(4-pyridinyl)pyrazolo[1,5-a]pyridin-3-yl]ethanone (0.68 g, 2.5 mmol) in toluene (10 mL) was added successively rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (100 mg, 0.15 mmol), cesium carbonate (1.2 g, 3.8 mmol), cyclopentylamine (1.5 mL, 12.5 mmol), and palladium (II) acetate (25 mg, 0.1 mmol). The resulting mixture was stirred at 90° C. for 24 hours, at which time the reaction was judged complete by thin layer chromatography. The solution was cooled to room temperature and ethyl acetate and water were added to the reaction mixture. The phases were separated, and the aquous phase again extracted with ethyl acetate. The combined organic phases were dried (magnesium sulfate), filtered and concentrated. The resulting residue was purified by flash chromatography (1:1 hexanes-ethyl acetate) to give 1-[7-(cyclopentylamino)-2-(4-pyridinyl)pyrazolo[1,5-a]pyridin-3-yl]ethanone (0.64 g, 80%) as a yellow foam. 1H NMR (CDCl3): δ 8.80 (d, 2H), 7.65 (d, 1H), 7.60 (d, 2H), 7.50 (t, 1H), 6.20 (d, 1H), 6.06 (d, 1H), 4.0 (m, 1H), 2.26 (s, 3H), 1.6–2.2 (m, 8H); MS m/z 321 (M+1).

Workup

  1. temperatureThe solution was cooled to room temperature
  2. customThe phases were separated
  3. extractionthe aquous phase again extracted with ethyl acetate
  4. dry with materialThe combined organic phases were dried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by flash chromatography (1:1 hexanes-ethyl acetate)

Sources & evidence

ORD record
ord-8f9e6fb9f7154338b7e04243ea210dc9
Source dataset
uspto-grants-2007_04
Patent number
US07199120B2

Reaction notes

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