Cyclopentylamine → HCID 18446641, compound

HRID 1269084Notes

Reaction equation

HRID 1269084 reaction equation
F[C:2]1[CH:7]=[C:6]([C:8]2[C:9]([C:17]3[N:18]=[C:19]([CH3:22])[S:20][CH:21]=3)=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)[CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH:29]1([NH2:34])[CH2:33][CH2:32][CH2:31][CH2:30]1>C(OCC)(=O)C>[CH:29]1([NH:34][C:2]2[CH:7]=[C:6]([C:8]3[C:9]([C:17]4[N:18]=[C:19]([CH3:22])[S:20][CH:21]=4)=[N:10][N:11]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=34)[CH:5]=[CH:4][N:3]=2)[CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

5

Reactant 3

HCID 2906CyclopentylamineHCID 11430Potassium CarbonateHCID 18446617HCID 18446617, compound

Product 1

HCID 18446641HCID 18446641, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-(2-fluoro-4-pyridinyl)-2-(2-methyl-1,3-thiazol-4-yl)pyrazolo[1,5-a]pyridine (220 mg, 0.71 mmol) and potassium carbonate (98 mg, 0.71 mmol) in cyclopentylamine (5 mL) was heated at 100° C. for 12 days. After cooling to room temperature, the solution was diluted with ethyl acetate and the organic phase was washed with water and brine, then dried over magnesium sulfate. Filtration and concentration, followed by flash chromatography (1:9 methanol/chloroform) gave N-cyclopentyl-4-[2-(2-methyl-1,3-thiazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyridinamine (265 mg, 100%) as an oil. 1H NMR (CDCl3): δ 8.49 (d, 1H), 8.04 (d, 1H), 7.49 (d, 1H), 7.08 (t, 1H), 6.74 (t, 1H), 6.59 (d, 1H), 6.43 (s, 1H), 5.44 (d, 1H), 3.79 (m, 1H), 2.73 (s, 3H), 1.92–1.42 (m, 8H). MS m/z 376 (M+1).

Workup

  1. washthe organic phase was washed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-1f8bb5b2ffd844a9a6b8eaf146eb5da4
Source dataset
uspto-grants-2007_04
Patent number
US07199120B2

Reaction notes

Loading…