Trifluoroacetic acid → 1-(2-Amino-2-methylpropyl)-3-(2-fluoro-4-(piperidin-4-ylmethyl)phenyl)urea

HRID 515296Notes

Reaction equation

HRID 515296 reaction equation
[NH2:1][C:2]([CH3:30])([CH3:29])[CH2:3][NH:4][C:5](=[O:28])[NH:6][C:7]1[CH:26]=[CH:25][C:10]([CH2:11][CH:12]2[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]2)=[CH:9][C:8]=1[F:27].FC(F)(F)C(O)=O>ClCCl>[NH2:1][C:2]([CH3:30])([CH3:29])[CH2:3][NH:4][C:5]([NH:6][C:7]1[CH:26]=[CH:25][C:10]([CH2:11][CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:9][C:8]=1[F:27])=[O:28]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86670947tert-Butyl 4-(4-(3-(2-amino-2-methylpropyl)ureido)-3-fluorobenzyl)piperidine-1-carboxylate

Product 1

HCID 671948621-(2-Amino-2-methylpropyl)-3-(2-fluoro-4-(piperidin-4-ylmethyl)phenyl)ureaYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(4-(3-(2-amino-2-methylpropyl)ureido)-3-fluorobenzyl)piperidine-1-carboxylate (2.272 mmol, 960 mg) was dissolved in dichloromethane (40 mL) and trifluoroacetic acid (45.4 mmol, 5181 mg) added. The mixture was stirred at room temperature for 3 hours before concentrating under reduced pressure. The resulting residue was purified by strong cation exchange column chromatography to afford the title compound (110 mg). MS (ESI) m/z 323.5 [M+H]+

Workup

  1. concentrationbefore concentrating under reduced pressure
  2. customThe resulting residue was purified by strong cation exchange column chromatography

Sources & evidence

ORD record
ord-a8657e6e425540aabb6c3af79829deaf
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

Loading…