Hydrochloric Acid → Octanedioic acid hydroxyamide [4-(2-amino-phenyl)-thiazol-2-yl]-amide

HRID 243622

Reaktionsgleichung

[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:11]=[C:12]([NH:15][C:16](=[O:34])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([NH:25][O:26]CC2C=CC=CC=2)=[O:24])[S:13][CH:14]=1)([O-])=O.Cl.Cl[Sn]Cl.[OH-].[Na+]>CO.O>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:11]=[C:12]([NH:15][C:16](=[O:34])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([NH:25][OH:26])=[O:24])[S:13][CH:14]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a mixture of compound 15 (0.040 g, 0.083 mmol) in methanol (2 ml) was added 1 ml of concentrated HCl. The suspension was cooled to 0° C. Then SnCl2 (0.094 g, 0.49 mmol) was added and the reaction mixture was stirred overnight at room temperature. The mixture was then diluted with 5 ml of water, adjusted to pH 10 with 5N NaOH and extracted with ethyl acetate (10 mL×3). The combined organic layers were washed with water, dried over K2CO3 and concentrated in vacuo. The crude product was purified by reverse phase HPLC to afford Octanedioic acid hydroxyamide [4-(2-amino-phenyl)-thiazol-2-yl]-amide 16 (0.016 g, 53% yield). NMR (400 MHz, DMSO-d6 cont 5% TFA) δ (ppm) 12.13 (1H, s), 7.56 (1H, d, J=7.0 Hz), 7.40 (1H, s), 7.09 (1H, t, J=7.0 Hz), 6.83 (1H, d, J=7.0 Hz), 6.72 (1H, m), 3.75-3.39 (4H, brs), 2.44 (2H, t, J=7.3 Hz), 2.29 (2H, t, J=7.3), 1.61 (2H, m), 1.51 (2H, m), 1.30 (4H, m).

Aufarbeitung

extractionextracted with ethyl acetate (10 mL×3)
washThe combined organic layers were washed with water
dry with materialdried over K2CO3
concentrationconcentrated in vacuo
customThe crude product was purified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag: ord-32b3aa34c9f442b7a2bcada762483e2d
Quelldatensatz: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08653278B2

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