Cyclopentylamine → N-Cyclopentyl-2-(methylsulfanyl)-7-phenylpyrazolo[1,5-a][1,3,5]triazin-4-amine

HRID 1296717Notes

Reaction equation

HRID 1296717 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:10]=[C:6]2[N:5]=[C:4]([S:17][CH3:18])[N:3]=1.[CH:19]1([NH2:24])[CH2:23][CH2:22][CH2:21][CH2:20]1>>[CH:19]1([NH:24][C:2]2[N:7]3[N:8]=[C:9]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[CH:10]=[C:6]3[N:5]=[C:4]([S:17][CH3:18])[N:3]=2)[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

3

Reactant 2

HCID 2906CyclopentylamineHCID 202498884-Chloro-2-(methylsulfanyl)-7-phenylpyrazolo[1,5-a][1,3,5]triazine

Product 1

HCID 69449600N-Cyclopentyl-2-(methylsulfanyl)-7-phenylpyrazolo[1,5-a][1,3,5]triazin-4-amineYield 78%

Conditions

Temperature
80 °C

Procedure

4-Chloro-2-(methylsulfanyl)-7-phenylpyrazolo[1,5-a][1,3,5]triazine (2.5 g, 9 mmol) was dissolved in cyclopentylamine (30 mL) and the resulting solution heated to 80° C. for 2 hours. Excess cyclopentylamine was removed in vacuo and the residue was dissolved in ethyl acetate. The organic phase was washed with water and brine, dried over magnesium sulfate, filtered and concentrated to give a foam. This foam was purified by silica gel chromatography (ethyl acetate:hexane 1:1) go give 2.3 g (78%) of N-cyclopentyl-2-(methylsulfanyl)-7-phenylpyrazolo[1,5-a][1,3,5]triazin-4amine as a solid. 1H-NMR (CDCl3): δ 7.96 (m, 2H), 7.47 (m, 3H), 6.63 (d, 1H), 6.56 (s,1H), 4.54 (m, 1H), 2.61 (s, 3H), 2.2–2.0 (m, 2H), 1.9–1.5 (m, 6H); MS m/z 326 (M+1).

Workup

  1. customExcess cyclopentylamine was removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a foam
  8. customThis foam was purified by silica gel chromatography (ethyl acetate:hexane 1:1)

Sources & evidence

ORD record
ord-e013aff31be94010b257727e9f8ae64d
Source dataset
uspto-grants-2007_07
Patent number
US07247626B2

Reaction notes

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