Trifluoroacetic acid → 2-{[4-(2-{[5-(4-Chlorophenyl)pyridin-2-yl]amino}ethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid hydrochloride

HRID 914395Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 914395
C([O:5][C:6](=[O:33])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)=[CH:22][N:21]=2)=O)[N:15]=1)([CH3:9])[CH3:8])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[ClH:32].[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([C:23]2[CH:24]=[CH:25][C:20]([NH:19][CH2:17][CH2:16][C:14]3[N:15]=[C:11]([S:10][C:7]([CH3:9])([CH3:8])[C:6]([OH:33])=[O:5])[S:12][CH:13]=3)=[N:21][CH:22]=2)=[CH:27][CH:28]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 673980322-{[4-(2-{[5-(4-Chlorophenyl)pyridin-2-yl]amino}-2-oxoethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester

Produkt 1

HCID 673988412-{[4-(2-{[5-(4-Chlorophenyl)pyridin-2-yl]amino}ethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid hydrochlorideAusbeute 102 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-{[4-(2-{[5-(4-Chlorophenyl)pyridin-2-yl]amino}-2-oxoethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester (145 mg) obtained in Example 242-3 was dissolved in dichloromethane (2 mL), trifluoroacetic acid (2 mL) was added, and the mixture was stirred at room temperature for 20 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; chloroform:methanol=20:1). The obtained compound was dissolved in diethyl ether (4 mL), 4 mol/L hydrochloric acid-ethyl acetate (0.5 mL) was added, and the mixture was stirred at room temperature for 1 hr. The precipitated solid was collected by filtration to give the title compound (69 mg) as a white solid.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel chromatography (elution solvent; chloroform:methanol=20:1)
  3. dissolutionThe obtained compound was dissolved in diethyl ether (4 mL)
  4. addition4 mol/L hydrochloric acid-ethyl acetate (0.5 mL) was added
  5. stirringthe mixture was stirred at room temperature for 1 hr
  6. filtrationThe precipitated solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-a24a98fa14144d23b00a56d2ee93f354
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026370B2

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