Thionyl Chloride → HCID 57799456, compound

HRID 2101345Notes

Reaction equation

HRID 2101345 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:31])[N:15]([CH2:17][C:18]4[C:19]([C:28]([OH:30])=O)=[N:20][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:23]=4)[N:16]=[C:10]3[C:9]=2[C:32]2[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=2)=[CH:4][CH:3]=1.S(Cl)([Cl:40])=O>C(Cl)CCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][N:11]3[C:14](=[O:31])[N:15]([CH2:17][C:18]4[C:19]([C:28]([Cl:40])=[O:30])=[N:20][C:21]([C:24]([F:26])([F:27])[F:25])=[CH:22][CH:23]=4)[N:16]=[C:10]3[C:9]=2[C:32]2[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 57799417HCID 57799417, compound

Product 1

HCID 57799456HCID 57799456, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirring solution of 3-((7-(4-chlorophenyl)-3-oxo-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-2(3H)-yl)methyl)-6-(trifluoromethyl)picolinic acid (71 mg, 0.133 mmol) in anhydrous ClCH2CH2Cl (1 mL) at room temperature was added dropwise thionyl chloride (2 mL). The mixture was then stirred at 80° C. for 1 h. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was evaporated with toluene (5 mL×2), and dried in high vacuum to afford the title compound (72 mg) as a yellow foam, which was used in the next reaction without further purification.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe residue was evaporated with toluene (5 mL×2)
  4. customdried in high vacuum

Sources & evidence

ORD record
ord-efbaa33dc43444c08d3c0875891456b2
Source dataset
uspto-grants-2009_08
Patent number
US07572808B2

Reaction notes

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