Phenacyl bromide → 3-[(2-Cycloheptylmethyl-5-naphthalen-2-yl-1H-pyrrole-3-carbonyl)-amino]-benzoic Acid

HRID 1018306

Reaktionsgleichung

Reaktionsgleichung von HRID 1018306
C(O[C:4](=[O:16])[CH2:5][C:6](=O)[CH2:7][CH:8]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)C.Br[CH2:18][C:19]([C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=1)=O.BrCC(C1C=CC=CC=1)=O.C([O:48][C:49](=[O:57])[C:50]1[CH:55]=[CH:54][CH:53]=[C:52]([NH2:56])[CH:51]=1)C1C=CC=CC=1.C[NH:59]C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O>O.O.O1CCOCC1>[CH:8]1([CH2:7][C:6]2[NH:59][C:19]([C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:22]=3)=[CH:18][C:5]=2[C:4]([NH:56][C:52]2[CH:51]=[C:50]([CH:55]=[CH:54][CH:53]=2)[C:49]([OH:48])=[O:57])=[O:16])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1

Komponenten

8

Edukt 5

HCID 6259Phenacyl bromideHCID 8567N-Methyl-D-glucamineHCID 691792-Bromo-2'-acetonaphthoneHCID 15428374Benzyl 3-aminobenzoateHCID 542125754-Cycloheptyl-3-oxo-butyric acid ethyl ester

Produkt 1

HCID 98907203-[(2-Cycloheptylmethyl-5-naphthalen-2-yl-1H-pyrrole-3-carbonyl)-amino]-benzoic Acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 218864351,4-Dioxane--water (1/1)Lösungsmittel

Versuchsvorschrift

The title compound was prepared according to the procedure of Example 1, using 4-cycloheptyl-3-oxo-butyric acid ethyl ester and 2-bromo-1-naphthalen-2-yl-ethanone instead of 4-adamantan-1-yl-3-oxo-butyric acid ethyl ester and 2-bromo-1-phenyl-ethanone in step a, and 3-amino-benzoic acid benzyl ester instead of 5-amino-isophthalic acid dibenzyl ester in step d. 1H NMR (300 MHz, d6-DMSO) 11.62 (1H, s), 9.64 (1H, s), 8.41 (1H, s), 8.14 (1H, s), 8.03 (1H, d), 7.94 (1H, d), 7.84 (3H, m), 7.60 (1H, m), 7.44 (3H, m), 7.34 (1H, s), 2.93 (2H, d), 1.98 (1H, br s), 1.67-1.22 (12H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 62.89; H, 7.51; N, 5.92%; C37H47N3O8.2.5 H2O requires: C, 62.87; H, 7.41; N, 5.94%.

Quellen und Nachweise

ORD-Eintrag
ord-470ab1d9d84940068c15a624cae842e3
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06479531B1

Verknüpfte Notizen

Wird geladen…