Water → 4-[N-(tert-butyl)-N-(tert-butyldimethylsilyloxy)amino]-N-(8-hydroxyquinolin-5-yl)-benzamide

HRID 498086Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 498086
[C:1]([N:5]([C:14]1[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=1)[O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl.[NH2:31][C:32]1[CH:41]=[CH:40][C:39]([OH:42])=[C:38]2[C:33]=1[CH:34]=[CH:35][CH:36]=[N:37]2.O>C(Cl)Cl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[C:1]([N:5]([C:14]1[CH:15]=[CH:16][C:17]([C:18]([NH:31][C:32]2[CH:41]=[CH:40][C:39]([OH:42])=[C:38]3[C:33]=2[CH:34]=[CH:35][CH:36]=[N:37]3)=[O:19])=[CH:21][CH:22]=1)[O:6][Si:7]([C:10]([CH3:13])([CH3:11])[CH3:12])([CH3:8])[CH3:9])([CH3:4])([CH3:2])[CH3:3]

Komponenten

8

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 113707224-[N-(tert-butyl)-N-(tert-butyldimethylsilyloxy)amino]-benzoic acidHCID 122537915-Aminoquinolin-8-ol hydrochloride

Produkt 1

HCID 223207184-[N-(tert-butyl)-N-(tert-butyldimethylsilyloxy)amino]-N-(8-hydroxyquinolin-5-yl)-benzamideAusbeute 35,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 0.15 g (0.464 mmol) of compound 2 in CH2Cl2 (2 mL) were added 0.11 g (0.561 mmol) of 1-(3-dimethylamino)propyl-3-ethylcarbodiimide hydrochloride, 0.03 g (0.232 mmol) of 4-dimethylaminopyridine, 2 mL of triethylamine, and 0.16 g (0.695 mmol) of 5-amino-8-hydroxyquinoline HCl salt. After stirring for 24 hours at room temperature, H2O and ethyl acetate were added. The organic layer was separated, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica, Hex:EtOAc=1:1) to give 0.076 g of compound 9 in 35% yield.

Aufarbeitung

  1. customThe organic layer was separated
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography (silica, Hex:EtOAc=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-2f8f8a81da3d4b2c91344163eb668f07
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06949654B2

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