Trifluoroacetic acid → 5-Methyl-2-[4-(piperidin-4-yloxy)phenyl]-2H-pyrazole-3-carboxylic acid cyclohexylamide

HRID 1013035Notes

Reaction equation

HRID 1013035 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]3[C:25]([C:26](=[O:34])[NH:27][CH:28]4[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]4)=[CH:24][C:23]([CH3:35])=[N:22]3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH:28]1([NH:27][C:26]([C:25]2[N:21]([C:18]3[CH:17]=[CH:16][C:15]([O:14][CH:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)=[CH:20][CH:19]=3)[N:22]=[C:23]([CH3:35])[CH:24]=2)=[O:34])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 589487744-[4-(5-Cyclohexylcarbamoyl-3-methylpyrazol-1-yl)phenoxy]piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 589487705-Methyl-2-[4-(piperidin-4-yloxy)phenyl]-2H-pyrazole-3-carboxylic acid cyclohexylamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[4-(5-cyclohexylcarbamoyl-3-methylpyrazol-1-yl)phenoxy]piperidine-1-carboxylic acid tert-butyl ester (482 mg, 1.00 mmol) in methylene chloride (10 mL) was added trifluoroacetic acid (2 mL). After the reaction was stirred at room temperature for 2 hours, it was quenched with saturated sodium bicarbonate and the aqueous layer was extracted with methylene chloride. The combined organic layers were dried (MgSO4) and concentrated to give the crude product in quantitative yield. LC-MS (C22H30N4O2 calculated 382) m/z 383 (M+H).

Workup

  1. customit was quenched with saturated sodium bicarbonate
  2. extractionthe aqueous layer was extracted with methylene chloride
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e547fd2845ed477abcc09f135fdee842
Source dataset
uspto-grants-2011_07
Patent number
US07981896B2

Reaction notes

Loading…