Cyclopentylamine → HCID 10128594, compound

HRID 1269041Notes

Reaction equation

HRID 1269041 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:23]3[CH:28]=[CH:27][N:26]=[C:25]([NH:29][CH:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)[N:24]=3)[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([NH:17][CH:18]4[CH2:22][CH2:21][CH2:20][CH2:19]4)[N:12]=3)=[C:6]2[CH:5]=[CH:4][CH:3]=1.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.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C.[CH:93]1([NH2:98])[CH2:97][CH2:96][CH2:95][CH2:94]1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH:93]1([NH:98][C:2]2[N:7]3[N:8]=[C:9]([C:23]4[CH:28]=[CH:27][N:26]=[C:25]([NH:29][CH:30]5[CH2:34][CH2:33][CH2:32][CH2:31]5)[N:24]=4)[C:10]([C:11]4[CH:16]=[CH:15][N:14]=[C:13]([NH:17][CH:18]5[CH2:22][CH2:21][CH2:20][CH2:19]5)[N:12]=4)=[C:6]3[CH:5]=[CH:4][CH:3]=2)[CH2:97][CH2:96][CH2:95][CH2:94]1

Participants

8

Reactant 5

HCID 2906CyclopentylamineHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 10127912HCID 10127912, compound

Product 1

HCID 10128594HCID 10128594, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

N-(4-{7-Chloro-2-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-3-yl}-2-pyrimidinyl)-N-cyclopentylamine (60 mg, 0.13 mmol) was dissolved in cyclopentylamine (4 mL). To this solution was added successively rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (31 mg, 0.05 mmol), cesium carbonate (61 mg, 0.18 mmol) and palladium (II) acetate (6 mg, 0.03 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 aqueous 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 20 mg (30%) of N-cyclopentyl-2,3-bis[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-7-amine as a foam. 1H NMR (CDCl3): δ 8.38 (d, 1H), 8.02 (broad s, 1H), 7.63 (d, 1H), 7.33 (t, 1H), 6.93 (s, 1H), 6.59 (d, 1H), 6.07 (d, 1H), 6.03 (m, 1H), 5.21 (m, 1H), 4.32 (m, 1H), 4.23 (m, 1H), 4.00 (m, 1H), 1.4–2.2 (m, 24H); MS m/z 524 (M+1).

Workup

  1. temperatureThe solution was cooled to room temperature
  2. customThe phases were separated
  3. extractionthe aqueous 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-0cc4a6e6c2f1452a86e89f8ee9fae4c8
Source dataset
uspto-grants-2007_04
Patent number
US07199120B2

Reaction notes

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