Water → HCID 90011212, compound

HRID 1481479Notes

Reaction equation

HRID 1481479 reaction equation
[CH3:1][N:2]1[C:6](=O)[O:5][C:4]([C:8]2[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[N:10]([C:17]3[CH:24]=[CH:23]C(C#N)=[CH:19][N:18]=3)[N:9]=2)=[N:3]1.CS(O)(=O)=O.[C:30]([O:33]CC)(=[O:32])[CH3:31].[OH2:36]>>[CH3:1][N:2]1[C:6](=[O:5])[O:36][C:4]([C:8]2[CH:12]=[C:11]([C:13]([F:14])([F:15])[F:16])[N:10]([C:17]3[CH:24]=[CH:23][C:31]([C:30]([OH:33])=[O:32])=[CH:19][N:18]=3)[N:9]=2)=[N:3]1

Participants

5

Reactant 4

HCID 962Water2×HCID 6395Methanesulfonic AcidHCID 8857Ethyl AcetateHCID 90011449HCID 90011449, compound

Product 1

HCID 90011212HCID 90011212, compoundYield 60%

Conditions

Temperature
70 °C

Procedure

Step-2: 5-6-(3-(4-Methyl-5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)-1H-pyrazol-1-yl)nicotinic acid: In a sealed tube containing a solution of 6-(3-(4-methyl-5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)-1H-pyrazol-1-yl)nicotinonitrile (0.80 g, 2.37 mmol) in methanesulfonic acid (5 mL, 77 mmol) and water (4 mL) was heated at 70° C. for 6 h. The reaction mixture was then cooled to room temperature and water (10 mL) was added to the above mixture followed by ethyl acetate (50 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with saturated aqueous NaHCO3 (30 mL), dried (Na2SO4) and filtered. The filtrate was rotary evaporated to afford 500 mg (60%) of the title compound as white solid. 1HNMR (400 MHz, DMSO-d6) δ 13.71 (s, 1H, D2O exchangeable), 9.01 (d, J=2.5 Hz, 1H), 8.55 (dd, J=2.5 & 8.5 Hz, 1H), 8.06 (d, J=8.5 Hz, 1H), 7.80 (s, 1H), 3.40 (s, 3H); ESI-MS (m/z) 356 (MH)+.

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (2×30 mL)
  4. washThe combined organic layers were washed with saturated aqueous NaHCO3 (30 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customThe filtrate was rotary evaporated

Sources & evidence

ORD record
ord-690bd10c8b1846818b3868470c0c202a
Source dataset
uspto-grants-2016_08
Patent number
US09409898B2

Reaction notes

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