Pyrrolidine → 1-[2-(4-Methoxyphenyl)-7-(1-pyrrolidinyl)pyrazolo[1,5-a]pyridin-3-yl]ethanone

HRID 861109Notes

Reaction equation

HRID 861109 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[C:10]([C:11](=[O:13])[CH3:12])=[C:6]2[CH:5]=[CH:4][CH:3]=1.[NH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1>>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:9]2[C:10]([C:11](=[O:13])[CH3:12])=[C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([N:22]4[CH2:26][CH2:25][CH2:24][CH2:23]4)[N:7]3[N:8]=2)=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 223500511-[7-(Chloro)-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]ethanone

Product 1

HCID 574947301-[2-(4-Methoxyphenyl)-7-(1-pyrrolidinyl)pyrazolo[1,5-a]pyridin-3-yl]ethanoneYield 84%

Procedure

In a similar manner as described in Example 1 from 1-[7-(chloro)-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]ethanone (5.00 g, 16.6 mmol) and pyrrolidine, 1-[2-(4-methoxyphenyl)-7-(1-pyrrolidinyl)pyrazolo[1,5-a]pyridin-3-yl]ethanone (4.68 g, 84%) was obtained as a yellow crystalline solid. 1H NMR (CDCl3): δ 7.79 (d, 1H), 7.50 (dd, 2H), 7.33 (t, 1H), 6.97 (dd, 2H), 6.12 (d, 1H), 3.84 (s, 3H), 3.74–3.70 (m, 4H), 2.11 (s, 3H), 1.99–1.95 (m, 4H); MS m/z 336 (M+1).

Sources & evidence

ORD record
ord-a420f48ce99a4e53bf19527243013b92
Source dataset
uspto-grants-2006_12
Patent number
US07153855B2

Reaction notes

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