Benzamidine, hydrochloride → 7-Chloro-2-(4-fluorophenyl)-3-(2-phenylpyrimidin-4-yl)pyrazolo[1,5-a]pyridine

HRID 1373839Notes

Reaction equation

HRID 1373839 reaction equation
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[C:10]([C:11](=O)[C:12]#[CH:13])=[C:6]2[CH:5]=[CH:4][CH:3]=1.Cl.[C:23]([NH2:31])(=[NH:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[O-]CC.[Na+]>C(O)C.O>[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[C:10]([C:11]3[CH:12]=[CH:13][N:31]=[C:23]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[N:30]=3)=[C:6]2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 80289Benzamidine, hydrochlorideHCID 2723922Sodium ethoxideHCID 219486831-[7-Chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-one

Product 1

HCID 102226467-Chloro-2-(4-fluorophenyl)-3-(2-phenylpyrimidin-4-yl)pyrazolo[1,5-a]pyridineYield 71%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 1-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-2-propyn-1-one (36 mg, 0.12 mmol) and benzamidine hydrochloride (25 mg, 0.16 mmol) in ethanol (500 μL) was added sodium ethoxide (52 μL, 3 M in ethanol, 0.16 mmol). The reaction mixture was stirred at room temperature 16 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine, then dried over magnesium sulfate. Filtration and concentration, followed by flash chromatography (3:1 hexanes-ethyl acetate) provided 7-chloro-2-(4-fluorophenyl)-3-(2-phenylpyrimidin-4-yl)pyrazolo[1,5-α]pyridine (34 mg, 71%). Rf 0.36 (3:1 hexanes-ethyl acetate); 1H NMR (CDCl3) δ 8.60–8.56 (m, 2H), 8.52–8.48 (m, 2H), 7.67 (m, 2H), 7.56–7.52 (m, 3H), 7.39 (m, 1H), 7.22–7.11 (m, 3H), 6.93 (d, 1H); 19F NMR (CDCl3) δ −112.30; MS m/z 401 (M+1).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-e1e18f1fb33146fca42c2dfb11c290e9
Source dataset
uspto-grants-2007_01
Patent number
US07163940B2

Reaction notes

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