Sodium Hydroxide → HCID 178520065, compound

HRID 2097612Notes

Reaction equation

HRID 2097612 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2C(=O)[O:12][N:11]=[C:10]2[C:15]2[C:19]([CH2:20][OH:21])=[N:18][O:17][N:16]=2)[CH:5]=[CH:6][C:7]=1[F:8].[OH-].[Na+]>CCO.O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:15]2[C:19]([CH2:20][OH:21])=[N:18][O:17][N:16]=2)=[N:11][OH:12])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 589418304-(3-Chloro-4-fluorophenyl)-3-[4-(hydroxymethyl)-1,2,5-oxadiazol-3-yl]-1,2,4-oxadiazol-5(4H)-one

Product 1

HCID 178520065HCID 178520065, compoundYield 87.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

4-(3-Chloro-4-fluorophenyl)-3-[4-(hydroxymethyl)-1,2,5-oxadiazol-3-yl]-1,2,4-oxadiazol-5(4H)-one (20 mg, 0.064 mmol) was dissolved in anhydrous EtOH (0.6 mL) followed by addition of 2 M of sodium hydroxide in water (60 μL). Reaction was stirred at 50° C. for 4 hrs. Consumption of starting material was monitored by TLC. The sample was quenched with acetic acid, diluted with MeOH and purified by preparative LCMS. The reaction was diluted with water and extracted with ethyl acetate three times, dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash silica column chromatography to yield the desired product (16 mg, 87%). 1H NMR (400 MHz, DMSO-d6) δ: 11.49 (s, 1H), 9.02 (s, 1H), 7.18 (dd, J=9.1, 9.1 Hz, 1H), 6.97 (dd, J=6.6, 2.7 Hz, 1H), 6.69 (m, 1H), 5.68 (t, J=6.2 Hz, 1H) 4.72 (d, J=5.8 Hz, 2H); MF═C10H8ClFN4O3; LCMS calculated for C10H9ClFN4O3 (M+H)+: m/z=287.035.

Workup

  1. customReaction
  2. customConsumption of starting material
  3. customThe sample was quenched with acetic acid
  4. additiondiluted with MeOH
  5. custompurified by preparative LCMS
  6. additionThe reaction was diluted with water
  7. extractionextracted with ethyl acetate three times
  8. dry with materialdried with sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe crude residue was purified by flash silica column chromatography

Sources & evidence

ORD record
ord-de280019ff2244d18b6e6646d28bfbc2
Source dataset
uspto-grants-2013_05
Patent number
US08450351B2

Reaction notes

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