Water → 7-(4-Chlorophenyl)-2-(4-(methylsufonyl)benzyl)-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3(2h)-one

HRID 2101318

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]3[C:14](=[O:17])[NH:15][N:16]=[C:10]3[C:9]=2[C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([S:38]([CH3:41])(=[O:40])=[O:39])=[CH:34][CH:33]=1.O>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]3[C:14](=[O:17])[N:15]([CH2:31][C:32]4[CH:33]=[CH:34][C:35]([S:38]([CH3:41])(=[O:40])=[O:39])=[CH:36][CH:37]=4)[N:16]=[C:10]3[C:9]=2[C:18]2[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirring solution of 7-(4-chlorophenyl)-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (16 mg, 0.05 mmol) in DMF (0.25 mL) at room temperature under argon was added K2CO3 (14 mg, 0.1 mmol), followed by 1-(chloromethyl)-4-(methylsulfonyl)benzene (11 mg, 0.0547 mmol). The reaction mixture was stirred at 70° C. for 10 min. After the reaction mixture was cooled to room temperature, water (2 mL) and EtOAc (5 mL) were added. The layers were separated. The organic layer was dried (MgSO4), filtered, and concentrated under reduced pressure to obtain crude product. This was purified by reverse phase preparative HPLC (without TFA) to isolate 14.5 mg of the title compound as a pale yellow solid. HPLC/MS: retention time=2.27 min, [M+H]+=491.

Workup

temperatureAfter the reaction mixture was cooled to room temperature
customThe layers were separated
dry with materialThe organic layer was dried (MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customto obtain crude product
customThis was purified by reverse phase preparative HPLC (without TFA)

Sources & evidence

ORD record: ord-7cc3eaac515c4a75b3e00355815b5697
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572808B2

Linked notes

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