Trifluoroacetic acid → N-(5-{5-[(2,3-dihydroxypropylamino)sulfonyl]-2-thienyl}-4-methyl-1,3-thiazol-2-yl)acetamide

HRID 1360868Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1360868
CC1(C)[O:6][CH:5]([CH2:7][NH:8][S:9]([C:12]2[S:16][C:15]([C:17]3[S:21][C:20]([NH:22][C:23](=[O:25])[CH3:24])=[N:19][C:18]=3[CH3:26])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH2:4][O:3]1.FC(F)(F)C(O)=O>C(Cl)Cl>[OH:6][CH:5]([CH2:4][OH:3])[CH2:7][NH:8][S:9]([C:12]1[S:16][C:15]([C:17]2[S:21][C:20]([NH:22][C:23](=[O:25])[CH3:24])=[N:19][C:18]=2[CH3:26])=[CH:14][CH:13]=1)(=[O:11])=[O:10]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 11998434N-[5-(5-[[(2,2-Dimethyl-1,3-dioxolan-4-YL)methyl]aminosulfonyl}-2-thienyl)-4-methyl-1,3-thiazol-2-YL]acetamide

Produkt 1

HCID 11998548N-(5-{5-[(2,3-dihydroxypropylamino)sulfonyl]-2-thienyl}-4-methyl-1,3-thiazol-2-yl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

N-[5-(5-{[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]aminosulfonyl}-2-thienyl)-4-methyl-1,3-thiazol-2-yl]acetamide (14) (48 mg; 0.11 mmol; 1 eq), is dissolved in DCM (5 ml). Trifluoroacetic acid (0.2 ml) is added and reaction mixture stirred at room temperature for 30 minutes. The solvents are evaporated and the crude product purified directly by preparative HPLC, affording Compound (17) as a white-off solid (7 mg; 16%). M− (ESI): 390.2; M+ (ESI): 392.2. HPLC (method A), Rt: 2.13 min (purity: 83.5%).

Aufarbeitung

  1. customreaction mixture
  2. customThe solvents are evaporated
  3. customthe crude product purified directly by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-27ae1fa9cce84176ad644f8376f94461
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879888B2

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