Trifluoroacetic acid → N-(4-methylthiazol-2-yl)-2-(piperazin-1-yl)acetamide

HRID 416727Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 416727
[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8](=[O:23])[CH2:9][N:10]2[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]2)[S:5][CH:6]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8](=[O:23])[CH2:9][N:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]2)[S:5][CH:6]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 57897251tert-Butyl 4-(2-(4-methylthiazol-2-ylamino)-2-oxoethyl)piperazine-1-carboxylate

Produkt 1

HCID 22164330N-(4-methylthiazol-2-yl)-2-(piperazin-1-yl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 4-(2-(4-methylthiazol-2-ylamino)-2-oxoethyl)piperazine-1-carboxylate (0.072 g, 0.21 mmol) in dichloromethane (2 ml) was added trifluoroacetic acid (2.5 ml). The reaction mixture was stirred at room temperature for 1.5 h, then the solvents were removed under reduced pressure to afford N-(4-methylthiazol-2-yl)-2-(piperazin-1-yl)acetamide (a semi-solid material) that was dried in vacuo. To a mixture of this material (supposedly 0.20 mmol) and isopropanol (3.5 ml) was added 2-amino-4,5-dichloro-3-nitropyridine (0.031 g, 0.15 mmol) followed by diisopropylethylamine (0.14 ml, 0.80 mmol). The reaction mixture was stirred at 45° C. for 20 h, then allowed to cool to room temperature and the solvents were removed in vacuo. The residue was absorbed on silica gel and the free running powder was placed on a 10 g isolute silica column which was eluted with 20% ethyl acetate in dichloromethane. The title compound was obtained as an orange solid (0.044 g, 54%). 1H-NMR (500 MHz, DMSO-d6) 2.26 (s, 3H, CH3), 2.65 (br s, 4H, piperazine N(CH2)2), 3.10 (br s, 4H, piperazine N(CH2)2), 3.33 (s, 2H, NCH2CO), 6.76 (s, 1H, thiazole 5-H), 6.96 (br s, 2H, NH2), 8.07 (s, 1H, 6-H), 11.75 (s, 1H, CONH);

Aufarbeitung

  1. customthe solvents were removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-935f55137c294f71b48481932ed19ef5
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088761B2

Notizen zur Reaktion

Wird geladen…