HCID 18446638, compound → HCID 10310134, compound

HRID 1269062Notes

Reaction equation

HRID 1269062 reaction equation
[CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([C:23]4[O:24][CH:25]=[CH:26][CH:27]=4)[C:15]([C:16]4[CH:21]=[CH:20][N:19]=[C:18](F)[CH:17]=4)=[C:11]3[CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>C1(N)CCCC1>[CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([C:23]4[O:24][CH:25]=[CH:26][CH:27]=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[CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 18446638HCID 18446638, compound

Product 1

HCID 10310134HCID 10310134, compoundYield 584.7%

Reagents, catalysts & solvents 1

HCID 2906CyclopentylamineSolvent

Procedure

N-Cyclopentyl-3-(2-fluoro-4-pyridinyl)-2-(2-furyl)pyrazolo[1,5-a]pyridin-7-amine (0.05 g, 0.02 mmol) was dissolved in cyclopentylamine (1 mL and heated) in a 135° C. oil bath for 4 days. The amine was removed in vacuo. The product was purified by silica gel chromatography (7:1 hexane:ethyl acetate) to give 25 mg (42%) of N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyridinyl]-2-(2-furyl)pyrazolo[1,5-a]pyridin-7-amine. 1H NMR (CDCl3) δ 8.1 (d, 1H), 7.51 (s, 1H), 7.17 (t, 1H), 6.94 (d, 1H), 6.69 (m, 2H), 6.5 (s, 1H), 6.45 (m, 1H), 6.00 (d, 1H). 5.95 (d, 1H), 4.6 (br d, 1H), 4.0 (m, 1H), 3.92 (m, 1H), 2.19–2.09 (m, 2H), 2.03–1.95 (m, 2H), 1.88–1.43 (m, 8H), 1.32–1.22 (m, 2H);MS m/z 428 (M+1).

Workup

  1. customThe amine was removed in vacuo
  2. customThe product was purified by silica gel chromatography (7:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-cc26623eb7a0452fa3b0988c727434da
Source dataset
uspto-grants-2007_04
Patent number
US07199120B2

Reaction notes

Loading…