Cyclohexyl isocyanide → 7-Bromo-4-(2,6-difluoro-benzyl)-2-ethyl-3-oxo-2,3,4,5-tetrahydro-benzo[f][1,4]oxazepine-5-carboxylic acid cyclohexylamide

HRID 1828691Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1828691
FC1C=CC=C(F)C=1CN.C1([N+]#[C-])CCCCC1.[CH:19]1([NH:25][C:26]([CH:28]2[C:34]3[CH:35]=[C:36]([Br:39])[CH:37]=[CH:38][C:33]=3[O:32][CH:31]([CH:40](C)[CH3:41])[C:30](=[O:43])[N:29]2[CH2:44][C:45]2[C:50]([F:51])=[CH:49][CH:48]=[CH:47][C:46]=2[F:52])=[O:27])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>CO>[CH:19]1([NH:25][C:26]([CH:28]2[C:34]3[CH:35]=[C:36]([Br:39])[CH:37]=[CH:38][C:33]=3[O:32][CH:31]([CH2:40][CH3:41])[C:30](=[O:43])[N:29]2[CH2:44][C:45]2[C:46]([F:52])=[CH:47][CH:48]=[CH:49][C:50]=2[F:51])=[O:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1

Komponenten

5

Edukt 3

HCID 79129Cyclohexyl isocyanideHCID 1235632,6-DifluorobenzylamineHCID 9958793HCID 9958793, Verbindung

Produkt 1

HCID 694892067-Bromo-4-(2,6-difluoro-benzyl)-2-ethyl-3-oxo-2,3,4,5-tetrahydro-benzo[f][1,4]oxazepine-5-carboxylic acid cyclohexylamideAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

2,6-Difluorobenzylamine (51 mg, 0.35 mmol) and cyclohexylisocyanide (39 mg, 0.36 mmol) were added to a solution of 2-(4-bromo-2-formyl-phenoxy)-butyric acid (prepared in analogy to 2-(4-bromo-2-formyl-phenoxy)-3-methyl-butyric acid [example 1] from ethyl 2-bromo-3-methyl butyrat, 100 mg, 0.35 mmol) in methanol (0.5 ml). After stirring for 2 h at r.t., the title compound was isolated (diastereomer 1 [inhibitorially active], retention time 2.09 min: 17.9 mg; diastereomer 2 [inhibitorially active], retention time 2.28 min, 7.3 mg, combined yield 14%, MS: m/e=521.1 [M+H+]) from the reaction mixture by reversed-phase, preparative HPLC (YMC CombiPrep C18 column 50×20 mm, solvent gradient 5–95% CH3CN in 0.1% TFA(aq) over 6.0 min, λ=230 nm, flow rate 40 ml/min).

Quellen und Nachweise

ORD-Eintrag
ord-0fbf9fb7a8b34e40999dbe67dca35567
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07060698B2

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