4-(2-Nitrophenyl)thiazole-2-amine → Octanedioic acid benzyloxy-amide [4-(2-nitro-phenyl)-thiazol-2-yl]-amide

HRID 243621

Reaktionsgleichung

COC(=O)CCCCCCC(NC1SC=C(C2C=CC=C([N+]([O-])=O)C=2)N=1)=O.[N+:28]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[C:37]1[N:38]=[C:39]([NH2:42])[S:40][CH:41]=1)([O-:30])=[O:29].[CH2:43]([O:50][NH:51][C:52]([CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][C:60](O)=[O:61])=[O:53])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>>[N+:28]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[C:37]1[N:38]=[C:39]([NH:42][C:60](=[O:61])[CH2:59][CH2:58][CH2:57][CH2:56][CH2:55][CH2:54][C:52]([NH:51][O:50][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[O:53])[S:40][CH:41]=1)([O-:30])=[O:29]

Komponenten

Edukt 3

HCID 5957794-(2-Nitrophenyl)thiazole-2-amine

HCID 11808064HCID 11808064, Verbindung

HCID 44550802octanedioic acid [4-(3-Nitro-phenyl)-thiazol-2-yl]-amide methyl ester

Produkt 1

HCID 89972899Octanedioic acid benzyloxy-amide [4-(2-nitro-phenyl)-thiazol-2-yl]-amide

Versuchsvorschrift

Compound 15 was prepared using the methodology described for the preparation of compound 14, by substituting 4-(3-nitrophenyl)-thiazol-2-ylamine with 4-(2-nitrophenyl)-2-thiazolamine (12) and using of compound 5 instead of compound 13. 1H NMR (400 MHz, DMSO-d6) δ (ppm). 12.14 (1H, s), 10.93 (1H, s); 7:88 (1H; d, J=7.4 Hz), 7.77 (1H, t, J=7.0 Hz), 7.72 (1H, d, J=7.4 Hz), 7.60 (1H, t, J=7.0 Hz), 7.51 (1H, s), 7.38-7.33 (5H, m), 4.78 (2H, s), 2.44 (2H, t, J=7.3 Hz), 1.94 (2H, t, J=7.3), 1.58 (2H, m), 1.49 (2H, m), 1.30-1.18 (4H, m).

Quellen und Nachweise

ORD-Eintrag: ord-8d27f26c5444460f80546e3eacc6b00c
Quelldatensatz: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08653278B2

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