Trifluoroacetic acid → 1-(Cyclopropylmethyl)-3-(4-(piperidin-4-yloxy)phenyl)urea

HRID 515271Notes

Reaction equation

HRID 515271 reaction equation
[CH:1]1([CH2:4][NH:5][C:6](=[O:28])[NH:7][C:8]2[CH:27]=[CH:26][C:11]([O:12][CH:13]3[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]3)=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[CH:1]1([CH2:4][NH:5][C:6]([NH:7][C:8]2[CH:27]=[CH:26][C:11]([O:12][CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)=[CH:10][CH:9]=2)=[O:28])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67193130tert-Butyl 4-(4-(3-(cyclopropylmethyl)ureido)phenoxy)piperidine-1-carboxylate

Product 1

HCID 671941431-(Cyclopropylmethyl)-3-(4-(piperidin-4-yloxy)phenyl)ureaYield 47.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of tert-butyl 4-(4-(3-(cyclopropylmethyl)ureido)phenoxy)piperidine-1-carboxylate (2.57 mmol, 1 g) in dichloromethane (10 mL) was added trifluoroacetic acid (2 mL). The resulting solution was stirred at room temperature for 30 minutes then was concentrated under vacuum. The residue was dissolved in dichloromethane and purified by SCX chromatography to give the title compound (350 mg). MS (ESI) m/z 290.1 [M+H]+

Workup

  1. concentrationthen was concentrated under vacuum
  2. dissolutionThe residue was dissolved in dichloromethane
  3. custompurified by SCX chromatography

Sources & evidence

ORD record
ord-30444f4f40f54c76a0755e2a2ebe9ba5
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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