Trifluoroacetic acid → 1-(Cyclopropylmethyl)-3-(4-(Piperazine-1-carbonyl)phenyl)urea

HRID 408864Notes

Reaction equation

HRID 408864 reaction equation
[CH:1]1([CH2:4][NH:5][C:6](=[O:29])[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][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:9]=[CH:10][C:11]([C:12]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)=[O:13])=[CH:27][CH:28]=2)=[O:29])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58055802tert-Butyl 4-(4-(3-(cyclopropylmethyl)ureido)benzoyl)piperazine-1-carboxylate

Product 1

HCID 580558061-(Cyclopropylmethyl)-3-(4-(Piperazine-1-carbonyl)phenyl)ureaYield 94.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(4-(3-(cyclopropylmethyl)ureido)benzoyl)piperazine-1-carboxylate (46.7 mmol, 18.78 g) was dissolved in dichloromethane (30 mL) and trifluoroacetic acid (233 mmol, 17.33 ml, 26.6 g) was added. The reaction was stirred for 1 hour and then was concentrated under reduced pressure. The crude material was triturated with ether to give a white powder after high vacuum drying. The white powder was taken up in water and carefully taken to pH 10 with sodium carbonate. The aqueous was then extracted with dichloromethane and the combined organic phases were dried, filtered and concentrated under reduced pressure to give the title compound (13.4 g).

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customThe crude material was triturated with ether
  3. customto give a white powder after high vacuum
  4. customdrying
  5. extractionThe aqueous was then extracted with dichloromethane
  6. customthe combined organic phases were dried
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e94b7fe153794c769b3b30cead44d5c1
Source dataset
uspto-grants-2014_06
Patent number
US08759352B2

Reaction notes

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