4-Methylmorpholine → 6-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)-N'-formylpyridazine-3-carbohydrazide

HRID 46199

Reaktionsgleichung

Reaktionsgleichung von HRID 46199
[Cl:1][C:2]1[CH:17]=[CH:16][C:15]([C@H:18]2[C@H:23]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C@@H:22]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C@H:21]([O:40][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C@@H:20]([CH2:48][O:49][CH2:50][C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[O:19]2)=[CH:14][C:3]=1[CH2:4][C:5]1[N:10]=[N:9][C:8](C(O)=O)=[CH:7][CH:6]=1.[CH:57]([NH:59][NH2:60])=[O:58].CCN=C=NCCCN(C)C.O.ON1C2C=CC=CC=2N=N1.CN1CC[O:87][CH2:86]C1>CN(C)C=O>[Cl:1][C:2]1[CH:17]=[CH:16][C:15]([C@H:18]2[C@H:23]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C@@H:22]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C@H:21]([O:40][CH2:41][C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)[C@@H:20]([CH2:48][O:49][CH2:50][C:51]3[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=3)[O:19]2)=[CH:14][C:3]=1[CH2:4][C:5]1[N:10]=[N:9][C:8]([C:57]([NH:59][NH:60][CH:86]=[O:87])=[O:58])=[CH:7][CH:6]=1

Komponenten

7

Edukt 5

HCID 79724-MethylmorpholineHCID 12229HydrazinecarboxaldehydeHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 672878076-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)pyridazine-3-carboxylic acid

Produkt 1

HCID 672870976-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)-N'-formylpyridazine-3-carbohydrazide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 6-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)pyridazine-3-carboxylic acid (1.4 mmol) from Step 1, formic hydrazide (107 mg, 1.8 mmol), EDCI (394 mg, 2.1 mmol), and 1-hydroxybenzotriazole hydrate (426 mg, 2.7 mmol) in N,N-dimethylformamide (15 mL) was added 4-methylmorpholine (0.45 mL, 4.1 mmol). The resulting mixture was stirred at ambient temperature overnight. After dilution with ethyl acetate, the organic layer was subsequently washed with water, hydrochloric acid (1.0 M), saturated sodium bicarbonate and brine prior to drying over magnesium sulfate. Filtration and removal of the volatiles under reduced pressure yielded titled compound as a glassy off-white amorphous solid, which was used without further purification.

Aufarbeitung

  1. washAfter dilution with ethyl acetate, the organic layer was subsequently washed with water, hydrochloric acid (1.0 M), saturated sodium bicarbonate and brine
  2. dry with materialto drying over magnesium sulfate
  3. filtrationFiltration and removal of the volatiles under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b5ff48d00fc64eb9859cf9f69c2f2f6e
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541380B2

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