Ethanol → HCID 67334655, compound

HRID 2102232Notes

Reaction equation

HRID 2102232 reaction equation
[CH:1]1([C:7]2[C:11]([CH2:12][C:13]3[CH:20]=[CH:19]C(C#N)=[CH:15][CH:14]=3)=[CH:10][N: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.[OH-:32].[K+].[CH2:34]([OH:36])[CH3:35]>O>[CH:1]1([C:7]2[C:11]([CH2:12][C:13]3[CH:20]=[CH:19][C:35]([C:34]([OH:32])=[O:36])=[CH:15][CH:14]=3)=[CH:10][N: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

Participants

5

Reactant 3

HCID 702Ethanol2×HCID 14797Potassium Hydroxide2×HCID 67335402HCID 67335402, compound

Product 1

HCID 67334655HCID 67334655, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a hot solution of 0.63 g 4-({3-cyclohexyl-1-[4-(trifluoromethoxy)phenyl]-1H-pyrazol-4-yl}methyl)benzonitrile From Step A above in 20 mL ethanol and 6 mL water was added 0.96 g potassium hydroxide. The resulting solution was refluxed under nitrogen for one day. HPLC showed some amide intermediate remaining. Add 1.05 g potassium hydroxide in 2 mL water and 4 mL ethanol. Reflux continued for another 17 hours. The solvents were removed under reduced pressure. The residue was re-suspended in 5 mL water and acidified with 18.0 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 7.93˜7.95 (m, 2), 7.91 (s, 1H), 7.75˜7.79 (m, 2H), 7.32˜7.36 (m, 4H), 3.95 (s, 2H), 2.60 (tt, J=3.2 & 11.8 Hz, 1H), 1.68˜1.81 (m, 5H), 1.51˜1.60 (m, 2H), 1.22˜1.36 (m, 3H). LC-MS: 2.51 min. (M+H=445.2).

Workup

  1. temperatureThe resulting solution was refluxed under nitrogen for one day
  2. temperatureReflux
  3. customThe solvents were removed under reduced pressure
  4. filtrationThe resulting solid was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-a62c1046480e4ded8b5f8c0802bd02d6
Source dataset
uspto-grants-2009_08
Patent number
US07572922B2

Reaction notes

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