Cyclopentylamine → N2,N4-dicyclopentyl-8-[2-(cyclopentylamino)-4-pyridinyl]-7-phenylpyrazolo[1,5-a][1,3,5]triazine-2,4-diamine

HRID 1296720Notes

Reaction equation

HRID 1296720 reaction equation
[CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:15]([C:16]4[CH:21]=[CH:20][N:19]=[C:18](F)[CH:17]=4)=[C:11]3[N:10]=[C:9](SC)[N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:31]1([NH2:36])[CH2:35][CH2:34][CH2:33][CH2:32]1>>[CH:31]1([NH:36][C:9]2[N:8]=[C:7]([NH:6][CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[N:12]3[N:13]=[C:14]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:15]([C:16]4[CH:21]=[CH:20][N:19]=[C:18]([NH:6][CH:1]5[CH2:5][CH2:4][CH2:3][CH2:2]5)[CH:17]=4)=[C:11]3[N:10]=2)[CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

3

Reactant 2

HCID 2906CyclopentylamineHCID 10151052N-cyclopentyl-8-(2-fluoro-4-pyridinyl)-2-(methylsulfanyl)-7-phenylpyrazolo[1,5-a][1,3,5]triazin-4-amine

Product 1

HCID 9828137N2,N4-dicyclopentyl-8-[2-(cyclopentylamino)-4-pyridinyl]-7-phenylpyrazolo[1,5-a][1,3,5]triazine-2,4-diamineYield 34%

Conditions

Temperature
160 °C

Procedure

N-Cyclopentyl-8-(2-fluoro-4-pyridiny)-2-(methylsulfanyl)-7-phenylpyrazolo[1,5-a][1,3,5]triazin -4amine 60 mg, 0.14 mmol) was dissolved in cyclopentylamine and heated at 160° C. in a glass pressure vessel for 24 hours. The resulting solution was concentrated in vacuo to give a residue that was purified by silica gel chromatography (ethyl acetate:hexane 1:1 to ethyl acetate) to yield 25 mg (34%) of N2,N4-dicyclopentyl-8-[2-(cyclopentylamino)-4-pyridinyl]-7-phenylpyrazolo[1,5-a][1,3,5]triazine-2,4-diamine as a foam. 1H-NMR (CDCl3): δ 7.94 (d, 1H), 7.60 (m, 2H), 7.45 (m, 3H), 6.81 (d, 1H), 6.36 (m, 1H), 5.13 (d, 1H), 4.60 (m, 1H), 4.44 (m, 2H), 3.74 (m, 1H), 2.1–1.4 (m, 24H); MS m/z 523 (M+1).

Workup

  1. concentrationThe resulting solution was concentrated in vacuo
  2. customto give a residue that
  3. customwas purified by silica gel chromatography (ethyl acetate:hexane 1:1 to ethyl acetate)

Sources & evidence

ORD record
ord-2ddcc18e9d3d4a59ade4e76aee306bd2
Source dataset
uspto-grants-2007_07
Patent number
US07247626B2

Reaction notes

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