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

HRID 1807710Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1807710
[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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 580558061-(Cyclopropylmethyl)-3-(4-(Piperazine-1-carbonyl)phenyl)ureaAusbeute 94,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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)

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-bcd8c24262f44bfeb0ea15561233e57d
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08357679B2

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