Hydrochloric Acid → HCID 21091512, Verbindung

HRID 1348583Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1348583
[NH2:1][C@@H:2]1[C:8](=[O:9])[N:7]([CH3:10])[C:6]2[CH:11]=[CH:12][CH:13]=[CH:14][C:5]=2[O:4][CH2:3]1.[F:15][C:16]([F:29])([C:25]([F:28])([F:27])[F:26])[CH2:17][NH:18][C:19](=[O:24])[CH2:20][C:21](O)=[O:22].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(C(C)C)CC)(C)C.Cl>O1CCCC1>[CH3:10][N:7]1[C:6]2[CH:11]=[CH:12][CH:13]=[CH:14][C:5]=2[O:4][CH2:3][C@H:2]([NH:1][C:21](=[O:22])[CH2:20][C:19]([NH:18][CH2:17][C:16]([F:29])([F:15])[C:25]([F:26])([F:28])[F:27])=[O:24])[C:8]1=[O:9]

Komponenten

8

Edukt 6

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 21072520HCID 21072520, VerbindungHCID 57471845(S)-7-amino-9-methyl-6,7-dihydro-9H-5-oxa-9-aza-benzocyclohepten-8-one

Produkt 1

HCID 21091512HCID 21091512, VerbindungAusbeute 39,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 0.06 g (0.31 mmol) (S)-7-amino-9-methyl-6,7-dihydro-9H-5-oxa-9-aza-benzocyclohepten-8-one in 5 ml tetrahydrofurane were added 0.07 g (0.31 mmol) N-(2,2,3,3,3-pentafluoro-propyl)-malonamic acid, 0.04 g (0.31 mmol) 1-hydroxybenzotriazole hydrate, 0.06 g (0.31 mmol) N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimid-hydrochloride and 0.1 ml (0.62 mmol) diisopropylethylamine. After stirring at room temperature over night the mixture was added to 1N aqueous hydrochloric acid. Extraction with dichloromethane, followed by washing with saturated aqueous sodium bicarbonate solution and drying with sodium sulfate, and chromatography on silicagel with ethylacetate/heptane yielded 0.05 g (39%) N-((S)-9-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl)-N′-(2,2,3,3,3-pentafluoro-propyl)-malonamide as white solid, MS m/e (%): 410.3 (M+H+, 100).

Aufarbeitung

  1. extractionExtraction with dichloromethane
  2. washby washing with saturated aqueous sodium bicarbonate solution
  3. dry with materialdrying with sodium sulfate, and chromatography on silicagel with ethylacetate/heptane

Quellen und Nachweise

ORD-Eintrag
ord-cd1c55957bbd49508baf3f27d39a6cdb
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07211573B2

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