Triethylamine → HCID 131724455, Verbindung

HRID 352246

Reaktionsgleichung

Reaktionsgleichung von HRID 352246
N[CH:2]1[CH2:6][CH2:5][CH:4]([N:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[C:12]([Cl:17])[C:11]=3[C:10]3=[N:18][O:19][C:20]([CH3:21])=[C:9]3[C:8]2=[O:22])[CH2:3]1.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH2:35][C:36]([OH:38])=O)[CH:28]=[C:29]([O:33][CH3:34])[C:30]=1[O:31][CH3:32].CC[N:41](CC)CC.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:17][C:12]1[C:11]2[C:10]3[C:9](=[C:20]([CH3:21])[O:19][N:18]=3)[C:8](=[O:22])[N:7]([C:4]3([C:29]4([O:33][CH3:34])[C:30]([O:31][CH3:32])=[C:25]([O:24][CH3:23])[CH:26]=[C:27]([CH2:35][C:36]([NH2:41])=[O:38])[CH2:28]4)[CH2:3][CH2:2][CH2:6][CH2:5]3)[C:16]=2[CH:15]=[CH:14][CH:13]=1

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 703723,4,5-Trimethoxyphenylacetic acidHCID 757711-HydroxybenzotriazoleHCID 22713955HCID 22713955, Verbindung

Produkt 1

HCID 131724455HCID 131724455, VerbindungAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirred solution of racemic 5-(3-aminocyclopentyl)-9-chloro-3-methyl-5H-isoxazolo[4,3-c]quinolin-4-one (81 mg, 0.26 mmol) in CH2Cl2 (3 mL) was added 3,4,5-trimethoxy phenyl acetic acid (114 mg, 0.52 mmol), Et3N (0.1 mL, 0.50 mmol), HOBt (41 mg, 0.3 mmol),DMAP (catalytic amount) and EDCI (72 mg, 0.38 mmol). The reaction mixture was stirred at r.t. for 18 hours. The mixture was diluted with CH2Cl2, washed (brine), dried (Na2SO4), filtered and concentrated. Column chromatography (silica gel, hexanes/ethyl acetate, gradient) gave the racemic title compound (89 mg, 66%). Mass Spectrum (FIA) (m/z) 454.0 (M+1)

Aufarbeitung

  1. washwashed (brine)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3f64bbca03c94c9d838d6d8d06135089
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06743794B2

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