Methanol → (R)-3-{3-[(benzo[1,2,5]thiadiazol-5-ylmethyl)-amino]-propyl}-5-(6-methoxyquinolin-4-yl)-oxazolidin-2-one

HRID 1725343

Reaktionsgleichung

Reaktionsgleichung von HRID 1725343
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:9][C@@H:8]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][CH:11]=2)[O:7][C:6]1=[O:22].[N:23]1[S:27][N:26]=[C:25]2[CH:28]=[C:29]([CH:32]=O)[CH:30]=[CH:31][C:24]=12.CO.[BH4-].[Na+]>C(OCC)(=O)C.C(Cl)Cl>[N:23]1[S:27][N:26]=[C:25]2[CH:28]=[C:29]([CH2:32][NH:1][CH2:2][CH2:3][CH2:4][N:5]3[CH2:9][C@@H:8]([C:10]4[C:19]5[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH3:21])[CH:18]=5)[N:13]=[CH:12][CH:11]=4)[O:7][C:6]3=[O:22])[CH:30]=[CH:31][C:24]=12

Komponenten

7

Edukt 4

HCID 887MethanolHCID 27762902,1,3-Benzothiadiazole-5-carbaldehydeHCID 4311764Sodium borohydrideHCID 68839629(R)-3-(3-amino-propyl)-5-(6-methoxy-quinolin-4-yl)-oxazolidin-2-one

Produkt 1

HCID 10003857(R)-3-{3-[(benzo[1,2,5]thiadiazol-5-ylmethyl)-amino]-propyl}-5-(6-methoxyquinolin-4-yl)-oxazolidin-2-oneAusbeute 66,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of (R)-3-(3-amino-propyl)-5-(6-methoxy-quinolin-4-yl)-oxazolidin-2-one (0.15 g, 0.5 mmol), benzo[1,2,5]thiadiazole-5-carbaldehyde (92 mg, 0.56 mmol), methanol (0.5 ml), methylene chloride (1.8 ml), 3 Å dry molecular sieve (1 g) was stirred at room temperature for 16 hours. Sodium borohydride (28 mg, 0.76 mmol) was added and the mixture was stirred for 3 hours. After concentration of the solvent the residue was dissolved in ethyl acetate and the organic phase was washed with water, dried over magnesium sulfate and concentrated. The residue was chromatographed on silicagel eluting with methylene chloride-methanol (99-1 first, then 90-10) to give (R)-3-{3-[(benzo[1,2,5]thiadiazol-5-ylmethyl)-amino]-propyl}-5-(6-methoxyquinolin-4-yl)-oxazolidin-2-one (150 mg, 59%).

Aufarbeitung

  1. customdry molecular sieve (1 g)
  2. stirringthe mixture was stirred for 3 hours
  3. washthe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silicagel
  7. washeluting with methylene chloride-methanol (99-1 first

Quellen und Nachweise

ORD-Eintrag
ord-d65bf6b1fa814a48a53b655c4022039c
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07491714B2

Verknüpfte Notizen

Wird geladen…