Trifluoroacetic acid → 1-(5-tert-Butyl-2-methyl-2H-pyrazol-3-yl)-3-[4-(piperidin-4-yloxy)-phenyl]-urea

HRID 499185Notes

Reaction equation

HRID 499185 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH:22]3[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]3)=[CH:17][CH:16]=2)=[O:13])[N:8]([CH3:10])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)=[CH:17][CH:16]=2)=[O:13])[N:8]([CH3:10])[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11634218HCID 11634218, compound

Product 1

HCID 594208831-(5-tert-Butyl-2-methyl-2H-pyrazol-3-yl)-3-[4-(piperidin-4-yloxy)-phenyl]-urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22 °C

Procedure

1-(5-tert-Butyl-2-methyl-2H-pyrazol-3-yl)-3-{4-[1-(tert-butoxy)carbonyl-piperidin-4-yloxy]phenyl}urea (Example 1. below, 2.25 g, 4.77 mmol) is suspended in a solution of trifluoroacetic acid in dichloromethane (25% v/v, 100 mL). The reaction mixture is stirred at 22° C. for 15 min. After removal of the solvent, the oily residue is neutralized with sodium hydroxide solution to pH 12 and extracted with dichloromethane (6×50 mL). The combined-organic phases are dried over anhydrous sodium sulfate and concentrated to yield a yellow solid (2.28 g, ES+(m/z) 372.1 [M+H]).

Workup

  1. customAfter removal of the solvent
  2. extractionextracted with dichloromethane (6×50 mL)
  3. dry with materialThe combined-organic phases are dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customto yield a yellow solid (2.28 g, ES+(m/z) 372.1 [M+H])

Sources & evidence

ORD record
ord-24a7a912673d4707b590bb41e976c6d0
Source dataset
uspto-grants-2010_08
Patent number
US07767674B2

Reaction notes

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