Thionyl Chloride → HCID 68586751, compound

HRID 2070897Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:9]([C:11]2[N:16]3[N:17]=[C:18]([NH:20][C:21]4[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=4)[N:19]=[C:15]3[CH:14]=[CH:13][CH:12]=2)O)[CH:6]=[CH:5][N:4]=1.S(Cl)([Cl:33])=O>C(Cl)(Cl)Cl>[Cl:33][CH:9]([C:7]1[CH:6]=[CH:5][N:4]=[C:3]([O:2][CH3:1])[CH:8]=1)[C:11]1[N:16]2[N:17]=[C:18]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)[N:19]=[C:15]2[CH:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

The reaction was performed in two batches of starting material (0.250 g and 0.324 g) according to the following procedure. The crude reaction mixtures were recombined and used in the subsequent step without additional purification or characterization. To a suspension of (2-methoxypyridin-4-yl)(2-(4-(trifluoromethyl)phenylamino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)methanol (0.324 g, 0.780 mmol) in chloroform (3.90 mL) at 0° C. was added dropwise thionyl chloride (0.153 mL, 2.090 mmol). The reaction was stirred at 0° C. for 45 min then at room temperature overnight. Additional thionyl chloride (0.05 mL) and reaction time (5 h) were necessary to drive the reaction to completion. The reaction was quenched with water and neutralized with sodium carbonate. 5-(Chloro(2-methoxypyridin-4-yl)methyl)-N-(4-(trifluoromethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine was obtained as a yellow oil not further purified or characterized. MS (ESI): m/z 434.2 [M+1]+.

Workup

customThe crude reaction mixtures
customused in the subsequent step without additional purification or characterization
customat room temperature
customovernight
customthe reaction to completion
customThe reaction was quenched with water and neutralized with sodium carbonate

Sources & evidence

ORD record: ord-a961b413b811408fa3a511af0d1b1fe1
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299056B2

Reaction notes

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