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

HRID 1807710Notes

Reaction equation

HRID 1807710 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) added. The reaction was stirred for 1 hour and then concentrated under reduced pressure. The crude material was triturated with ether to give a white powder after high vacuum drying, which was taken up in water and carefully taken to pH 10 with sodium carbonate. The aqueous was 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. concentrationconcentrated 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 extracted with dichloromethane
  6. customthe combined organic phases were dried
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bcd8c24262f44bfeb0ea15561233e57d
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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