Water → HCID 67335127, compound

HRID 1669835Notes

Reaction equation

HRID 1669835 reaction equation
[CH:1]1([N:7]2[C:11]([CH2:12][C:13]3[CH:20]=[CH:19][C:16]([C:17]#N)=[CH:15][CH:14]=3)=[CH:10][C:9]([C:21]3[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=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]([CH2:12][C:13]3[CH:20]=[CH:19][C:16]([C:17]([OH:33])=[O:32])=[CH:15][CH:14]=3)=[CH:10][C:9]([C:21]3[CH:26]=[CH:25][C:24]([O:27][C:28]([F:29])([F:30])[F:31])=[CH:23][CH:22]=3)=[N:8]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 67334339HCID 67334339, compound

Product 1

HCID 67335127HCID 67335127, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 0.395 g 4-({1-cyclohexyl-3-[4-(trifluoromethoxy)phenyl]-1H-pyrazol-5-yl}methyl)benzonitrile from Step A above in 9 mL ethanol and 3 mL water was added 0.80 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 14 mL 1 N HCl to the residue. The title compound was collected by filtrated, washed with water several times, and dried to give a off-white solid. 1H NMR (CD3OD, 600 MHz) δ 7.97 (d, J=8.2 Hz, 2H), 7.81˜7.84 (m, 2H), 7.35 (d, J=8.2 Hz, 2H), 7.25 (d, J=8.2 Hz, 2H), 6.425 (s, 1H), 4.165 (s, 2H), 4.01 (tt, J=3.9 & 11.8 Hz, 1H), 1.86˜1.93 (m, 2H), 1.78˜1.83 (m, 2H), 1.64˜1.68 (m, 3H), 1.20˜1.35 (m, 3H). LC-MS: 2.49 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 14 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 off-white solid
  10. custom2.49 min. (M+H=445.2)

Sources & evidence

ORD record
ord-acd7d65d03b343b7b423b9ced5632213
Source dataset
uspto-grants-2011_08
Patent number
US07989475B2

Reaction notes

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