Water → HCID 67334871, compound

HRID 2102229Notes

Reaction equation

HRID 2102229 reaction equation
[CH:1]1([C:7]2[N: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)[N:10]=[CH:9][C:8]=2[CH2:23][C:24]2[CH:31]=[CH:30][C:27]([C:28]#N)=[CH:26][CH:25]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH2:32].[OH-:33].[K+]>C(O)C>[CH:1]1([C:7]2[N:11]([C:12]3[CH:13]=[CH:14][C:15]([O:18][C:19]([F:20])([F:21])[F:22])=[CH:16][CH:17]=3)[N:10]=[CH:9][C:8]=2[CH2:23][C:24]2[CH:31]=[CH:30][C:27]([C:28]([OH:33])=[O:32])=[CH:26][CH:25]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 67335137HCID 67335137, compound

Product 1

HCID 67334871HCID 67334871, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a hot solution of 0.73 g 4-({5-cyclohexyl-1-[4-(trifluoromethoxy)phenyl]-1H-pyrazol-4-yl}methyl)benzonitrile From Step E above in 15 mL ethanol and 6 mL water was added 1.11 g potassium hydroxide. The resulting solution was refluxed under nitrogen over night. The solvents were removed under reduced pressure. The residue was re-suspended in 10 mL water and acidified with 9.0 mL 2 N HCl. The resulting solid was filtered, washed with water, and dried to give the title compound as a white solid. 1H NMR (CD3OD, 500 MHz) δ 7.95 (d, J=8.2 Hz, 2H), 7.48˜7.50 (m, 2H), 7.45 (d, J=8.6 Hz, 2H), 7.36 (s, 1H), 7.32 (d, J=8.2 Hz, 2H), 4.06 (s, 2H), 2.66 (tt, J=3.0 & 12.7 Hz, 1H), 1.69˜1.73 (m, 4H), 1.53˜1.64 (m, 3H), 1.09˜1.19 (m, 3). LC-MS: 2.29 min. (M+H=445.2).

Workup

  1. temperatureThe resulting solution was refluxed under nitrogen over night
  2. customThe solvents were removed under reduced pressure
  3. filtrationThe resulting solid was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-da68c0b3b7d64055bf3edaefb1f7d1df
Source dataset
uspto-grants-2009_08
Patent number
US07572922B2

Reaction notes

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