Water → HCID 67334872, compound

HRID 1669841Notes

Reaction equation

HRID 1669841 reaction equation
C1([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)CCCCC1.[OH2:32].[OH-:33].[K+]>C(O)C>[CH2:12]1[CH2:17][CH:16]([CH:23]([C:24]2[CH:31]=[CH:30][C:27]([C:28]([OH:33])=[O:32])=[CH:26][CH:25]=2)[C:8]2[CH:9]=[N:10][N:11]([C:12]3[CH:13]=[CH:14][C:15]([O:18][C:19]([F:22])([F:20])[F:21])=[CH:16][CH:17]=3)[CH:7]=2)[CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 67335137HCID 67335137, compound

Product 1

HCID 67334872HCID 67334872, 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, 3H). 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-2622226468db40eda3d4d3aa1763db79
Source dataset
uspto-grants-2011_08
Patent number
US07989475B2

Reaction notes

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