Trifluoroacetic acid → 1-Cyclobutyl-3-(2-fluoro-4-(piperazine-1-carbonyl)phenyl)urea

HRID 408872Notes

Reaction equation

HRID 408872 reaction equation
[CH:1]1([NH:5][C:6](=[O:30])[NH:7][C:8]2[CH:28]=[CH:27][C:11]([C:12]([N:14]3[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]3)=[O:13])=[CH:10][C:9]=2[F:29])[CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[CH:1]1([NH:5][C:6]([NH:7][C:8]2[CH:28]=[CH:27][C:11]([C:12]([N:14]3[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]3)=[O:13])=[CH:10][C:9]=2[F:29])=[O:30])[CH2:2][CH2:3][CH2:4]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58055805tert-Butyl 4-(4-(3-cyclobutylureido)-3-fluorobenzoyl)piperazine-1-carboxylate

Product 1

HCID 666611341-Cyclobutyl-3-(2-fluoro-4-(piperazine-1-carbonyl)phenyl)ureaYield 7.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(4-(3-cyclobutylureido)-3-fluorobenzoyl)piperazine-1-carboxylate (2.8 g, 66.67 mmol), trifluoracetic acid and dichloromethane were stirred for 20 hours then concentrated under reduced pressure. The residue was taken up in dichloromethane/methanol, loaded on to a strong cation exchange column and washed with dichloromethane/methanol. Elution of the column with 2M ammonia in methanol gave the title compound (1.6 g). MS (ESI) m/z: 321.4 [M+H]+

Workup

  1. concentrationthen concentrated under reduced pressure
  2. washwashed with dichloromethane/methanol
  3. washElution of the column with 2M ammonia in methanol

Sources & evidence

ORD record
ord-b6fb0a7f9661469b9fe7e0fde0ba746a
Source dataset
uspto-grants-2014_06
Patent number
US08759352B2

Reaction notes

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