Acetic Acid → 2-[4-(1-Cyclopentylpiperidin-4-yloxy)phenyl]-5-methyl-2H-pyrazole-3-carboxylic acid cyclohexylamide

HRID 598778Notes

Reaction equation

HRID 598778 reaction equation
[CH:1]1([NH:7][C:8]([C:10]2[N:11]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH:23]4[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]4)=[CH:18][CH:17]=3)[N:12]=[C:13]([CH3:15])[CH:14]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:29]1(=O)[CH2:33][CH2:32][CH2:31][CH2:30]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH:1]1([NH:7][C:8]([C:10]2[N:11]([C:16]3[CH:17]=[CH:18][C:19]([O:22][CH:23]4[CH2:24][CH2:25][N:26]([CH:29]5[CH2:33][CH2:32][CH2:31][CH2:30]5)[CH2:27][CH2:28]4)=[CH:20][CH:21]=3)[N:12]=[C:13]([CH3:15])[CH:14]=2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8452CyclopentanoneHCID 5049666Sodium triacetoxyborohydrideHCID 589487705-Methyl-2-[4-(piperidin-4-yloxy)phenyl]-2H-pyrazole-3-carboxylic acid cyclohexylamide

Product 1

HCID 247845672-[4-(1-Cyclopentylpiperidin-4-yloxy)phenyl]-5-methyl-2H-pyrazole-3-carboxylic acid cyclohexylamideYield 3.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-methyl-2-[4-(piperidin-4-yloxy)phenyl]-2H-pyrazole-3-carboxylic acid cyclohexylamide (60 mg, 0.157 mmol) in methylene chloride (9 mL) was added cyclopentanone (21 μL, 0.24 mmol) and acetic acid (150 μL). After 1 hour at room temperature, sodium triacetoxyborohydride (51 mg, 0.24 mmol) was added and the reaction was allowed to stir for an additional 4 hours. The reaction was quenched with 10% NaOH and extracted with methylene chloride. The methylene chloride solution was dried (MgSO4) and concentrated. The residue was purified by semi-prep LC-MS to give 2.4 mg of the desired product. LC-MS (C27H38N4O2 calculated 450) m/z 451 (M+H); 1H NMR (300 MHz, CDCl3) 7.34-7.31 (m, 2H), 7.01-6.98 (m, 2H), 6.78 (d, J=8.4 Hz, 1H), 6.70 (s, 1H), 4.42 (m, 1H), 3.95-3.93 (m, 1H), 2.87-2.83 (m, 2H), 2.68-2.54 (m, 3H), 2.23 (s, 3H), 2.15-1.14 (m, 22H).

Workup

  1. customThe reaction was quenched with 10% NaOH
  2. extractionextracted with methylene chloride
  3. dry with materialThe methylene chloride solution was dried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by semi-prep LC-MS

Sources & evidence

ORD record
ord-2e78423c969442f98f9bf61173cb26be
Source dataset
uspto-grants-2011_03
Patent number
US07897634B2

Reaction notes

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