Diethylamine → N,N-diethyl-2-(4-fluorophenyl)-3-(4-pyridinyl)pyrazolo[1,5-a]pyridin-7-amine

HRID 1373832Notes

Reaction equation

HRID 1373832 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]([NH:26][CH2:27][CH3:28])[CH3:25]>>[CH2:24]([N:26]([CH2:27][CH3:28])[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)[CH3:25]

Participants

3

Reactant 2

HCID 8021DiethylamineHCID 98584077-Chloro-2-(4-fluorophenyl)-3-(4-pyridinyl)pyrazolo[1,5-a]pyridine

Product 1

HCID 9946990N,N-diethyl-2-(4-fluorophenyl)-3-(4-pyridinyl)pyrazolo[1,5-a]pyridin-7-amine

Procedure

7-Chloro-2-(4-fluorophenyl)-3-(4-pyridinyl)pyrazolo[1,5-α]pyridine and excess of diethylamine in alcohol (1 mL) in sealed tube was heated at 120° C. for overnight. The mixture was evaporated to dryness and purified by preparative thin layer chromatography to give N,N-diethyl-2-(4-fluorophenyl)-3-(4-pyridinyl)pyrazolo[1,5-α]pyridin-7-amine. 1H NMR (CDCl3): δ 8.61 (d, 2H, J=6.0 Hz), 7.61–7.66 (m, 2H), 7.22–7.34 (m, 4H), 7.09 (t, 2H, J=8.7 Hz), 6.32 (d, 1H, J=6.1 Hz), 3.64 (q, 4H, J=7.0 Hz), 1.26 (t, 6H, J=7 Hz). MS (ES+ve): 362 (25, M+2), 361 (100, M+1).

Workup

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

Sources & evidence

ORD record
ord-e17679c5b5944c408a19219cb7f5021d
Source dataset
uspto-grants-2007_01
Patent number
US07163940B2

Reaction notes

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