Acetic Acid → HCID 22262577, compound

HRID 1167571Notes

Reaction equation

HRID 1167571 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[NH:11][N:10]=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=3)[C:8]=2[C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)[CH2:3][CH2:2]1.CC(O)=O.[OH-].[Na+].[CH3:34][C:35]([CH3:37])=O>>[CH3:34][CH:35]([N:1]1[CH2:6][CH2:5][CH:4]([C:7]2[NH:11][N:10]=[C:9]([C:12]3[CH:13]=[CH:14][C:15]([C:18]([F:20])([F:19])[F:21])=[CH:16][CH:17]=3)[C:8]=2[C:22]2[CH:23]=[CH:24][N:25]=[CH:26][CH:27]=2)[CH2:3][CH2:2]1)[CH3:37]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 14798Sodium HydroxideHCID 22037547HCID 22037547, compound

Product 1

HCID 22262577HCID 22262577, compound

Procedure

To a solution of 5-(4-piperidyl)-4-(4-pyridyl)-3-[4-(trifluoromethyl)phenyl]pyrazole (Example C-83) (300 mg, 0.7 mmol) in 50 mL of acetone was added 1 mL of AcOH and NaBH(OAc), (15 g, 70.8 mmol). The mixture was warmed to reflux and was stirred for 5 days. The reaction mixture was poured onto 100 mL of 2.5 N NaOH and was extracted with ethyl acetate (2×100 mL). The extracts were combined and washed with brine (1×100 mL). The organic phase was dried over Na2SO4, filtered, and concentrated to afford the title compound: MS (M+H): 415 (base peak).

Workup

  1. temperatureThe mixture was warmed
  2. temperatureto reflux
  3. extractionwas extracted with ethyl acetate (2×100 mL)
  4. washwashed with brine (1×100 mL)
  5. dry with materialThe organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-86f23872af7d484cadd59454e0e3e37d
Source dataset
uspto-grants-2003_09
Patent number
US06617324B1

Reaction notes

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