Hydrochloric Acid → HCID 69093424, compound

HRID 2174297Notes

Reaction equation

HRID 2174297 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[C:9]([C:10]#N)=[N:8][C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[N:6]1.[C:22](=O)([O-])[O-:23].[Cs+].[Cs+].Cl.C[OH:30]>>[F:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[C:9]([C:10]([O:23][CH3:22])=[O:30])=[N:8][C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[N:6]1

Participants

5

Reactant 4

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 10796Cesium carbonateHCID 69093841HCID 69093841, compound

Product 1

HCID 69093424HCID 69093424, compoundYield 99%

Procedure

To a solution of 1-(2-fluorobenzyl)-3-(pyridin-2-yl)-1H-1,2,4-triazole-5-carbonitrile (I-33, 120 mg, 0.430 mmol) in methanol (2.0 mL) was added cesium carbonate (280 mg, 0.859 mmol). After stirring at room temperature for 3.75 h, aqueous 0.1 N hydrochloric acid (10 mL) was added, followed by aqueous 1 N hydrochloric acid (˜1 mL) until pH ˜3. After stirring for 45 min, the methanol was removed in vacuo, and the crude residue was brought up in ethyl acetate (75 mL) and saturated aqueous sodium bicarbonate (50 mL). The layers were separated, and the aqueous layer was extracted with ethyl acetate (2×50 mL). The organics were washed with brine (50 mL), dried over magnesium sulfate, filtered, and the solvent was removed in vacuo to give the crude product as white solid. Purification by silica gel chromatography (20-80% ethyl acetate in hexanes) gave methyl 1-(2-fluorobenzyl)-3-(pyridin-2-yl)-1H-1,2,4-triazole-5-carboxylate (99% yield) as a white solid.

Workup

  1. stirringAfter stirring for 45 min
  2. customthe methanol was removed in vacuo
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (2×50 mL)
  5. washThe organics were washed with brine (50 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent was removed in vacuo
  9. customto give the crude product as white solid
  10. customPurification by silica gel chromatography (20-80% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-5cc446495c764c379b420f0506814239
Source dataset
uspto-grants-2015_06
Patent number
US09061030B2

Reaction notes

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