Butylamine → N-butyl-2-(4-fluorophenyl)-3-pyridin-4-ylpyrazolo[1,5-a]pyridin-7-amine

HRID 1373835Notes

Reaction equation

HRID 1373835 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)=[C:6]2[CH:5]=[CH:4][CH:3]=1.[CH2:24]([NH2:28])[CH2:25][CH2:26][CH3:27]>C1(C)C=CC=CC=1>[CH2:24]([NH:28][C:2]1[N:7]2[N:8]=[C:9]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)=[C:6]2[CH:5]=[CH:4][CH:3]=1)[CH2:25][CH2:26][CH3:27]

Participants

4

Reactant 2

HCID 8007ButylamineHCID 98584077-Chloro-2-(4-fluorophenyl)-3-(4-pyridinyl)pyrazolo[1,5-a]pyridine

Product 1

HCID 10155439N-butyl-2-(4-fluorophenyl)-3-pyridin-4-ylpyrazolo[1,5-a]pyridin-7-amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of of 7-chloro-2-(4-fluorophenyl)-3-(4-pyridinyl)pyrazolo[1,5-α]pyridine in toluene (2 mL) and excess of butylamine (1 mL) in sealed tube was heated at 110° C. for overnight. The mixture was evaporated to dryness and purified by preparative thin layer chromatography to give N-butyl-2-(4-fluorophenyl)-3-pyridin-4-ylpyrazolo[1,5-α]pyridin-7-amine. 1H NMR (CDCl3): δ 8.53 (d, 2H, J=5.1 Hz), 7.54–7.57 (m, 2H), 7.20–7.24 (m, 3H), 7.06 (t, 2H, J=8.6 Hz), 7.02–7.00 (m, 1H), 6.04 (bs, 1H), 5.95 (d, 1H, J=7.7 Hz), 3.39 (q, 2H, J=6.4 Hz), 1.74–1.78 (m, 2H), 1.47–1.56 (m, 2H), 0.99 (t, 3H, J=7.4 Hz); MS m/z 361 (M+1).

Workup

  1. customThe mixture was evaporated to dryness
  2. custompurified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-2ad218d0002c40918787f6c40795a313
Source dataset
uspto-grants-2007_01
Patent number
US07163940B2

Reaction notes

Loading…