Water → HCID 67335173, compound

HRID 1669833Notes

Reaction equation

HRID 1669833 reaction equation
[CH:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=3)=[CH:10][C:9]([CH2:23][C:24]3[CH:31]=[CH:30][C:27]([C:28]#N)=[CH:26][CH:25]=3)=[N:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH2:32].[OH-:33].[K+]>C(O)C>[CH:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=3)=[CH:10][C:9]([CH2:23][C:24]3[CH:25]=[CH:26][C:27]([C:28]([OH:33])=[O:32])=[CH:30][CH:31]=3)=[N:8]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 67335072HCID 67335072, compound

Product 1

HCID 67335173HCID 67335173, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a warm solution of 0.45 g 4-({1-cyclohexyl-5-[4-(trifluoromethoxy)phenyl]-1H-pyrazol-3-yl}methyl)benzonitrile from Step D above in 10 mL ethanol and 2.5 mL water was added 0.70 g potassium hydroxide pellets. The resulting solution was refluxed under nitrogen over night. Ethanol was removed under reduced pressure. The product was precipitated by adding 11.5 mL 1 N HCl to the residue. The title compound was collected by filtrated, washed with water several times, and dried to give a slightly yellowish solid. 1H NMR (CD3OD, 500 MHz) δ 7.94˜7.96 (m, 2H), 7.47˜7.49 (m, 2H), 7.37˜7.41 (m, 4H), 6.09 (s, 1H), 4.06 (s, 2H), 4.05 (tt, J=3.8 & 11.9 Hz, 1H), 1.97˜2.05 (m, 2H), 1.85˜1.93 (m, 4H), 1.67˜1.71 (m, 1H), 1.26˜1.36 (m, 3H). LC-MS: 2.38 min. (M+H=445.2).

Workup

  1. temperatureThe resulting solution was refluxed under nitrogen over night
  2. customEthanol was removed under reduced pressure
  3. customThe product was precipitated
  4. additionby adding 11.5 mL 1 N HCl to the residue
  5. customThe title compound was collected
  6. filtrationby filtrated
  7. washwashed with water several times
  8. customdried
  9. customto give a slightly yellowish solid
  10. custom2.38 min. (M+H=445.2)

Sources & evidence

ORD record
ord-4851572f060242dc982da059445367aa
Source dataset
uspto-grants-2011_08
Patent number
US07989475B2

Reaction notes

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