Cyclopentylamine → HCID 10238131, compound

HRID 1269075Notes

Reaction equation

HRID 1269075 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:23]3[O:24][CH:25]=[CH:26][CH:27]=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.C(OCC)(=O)C.[CH:34]1([NH2:39])[CH2:38][CH2:37][CH2:36][CH2:35]1>>[CH:34]1([NH:39][C:2]2[N:7]3[N:8]=[C:9]([C:23]4[O:24][CH:25]=[CH:26][CH:27]=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)[CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

4

Reactant 3

HCID 2906CyclopentylamineHCID 8857Ethyl AcetateHCID 18446623HCID 18446623, compound

Product 1

HCID 10238131HCID 10238131, compoundYield 91%

Conditions

Temperature
100 °C

Procedure

4-[7-Chloro-2-(2-furyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine (200 mg, 0.53 mmol) was dissolved in 5 mL of cyclopentylamine. The solution was heated at 100° C. overnight, then cooled to room temperature. Ethyl acetate was added to dilute the reaction mixture, the organic phase was washed with water and brine and dried over magnesium sulfate. Filtration and concentration followed by purification with flash chromatography (1:4 ethyl acetate:hexanes) gave N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(2-furyl)pyrazolo[1,5-a]pyridin-7-amine (206 mg, 91%) as a yellow solid. 1H NMR (CDCl3): δ 8.20 (d, 1H), 7.68 (d, 1H), 7.62 (d, 1H), 7.32 (t, 1H), 6.92 (d, 1H), 6.59 (m, 2H), 6.05 (m, 2H), 5.11 (d, 1H), 4.43 (m, 1H), 4.04 (m, 1H), 2.14 (m, 4H), 1.87–1.56 (m, 12H). MS m/z 429 (M+1).

Workup

  1. temperaturecooled to room temperature
  2. additionto dilute the reaction mixture
  3. washthe organic phase was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationFiltration and concentration
  6. customfollowed by purification with flash chromatography (1:4 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-7b9b6c87b18343268b08cea0e1f35552
Source dataset
uspto-grants-2007_04
Patent number
US07199120B2

Reaction notes

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