2(1H)-Quinoxalinone, 3,4-dihydro- → tert-butyl N-(3-(1,2,3,4-tetrahydroquinoxalin-3-on-1-carbonyl)benzyl)-N-methylcarbamate

HRID 901963

Reaktionsgleichung

Reaktionsgleichung von HRID 901963
CCN=C=NCCCN(C)C.Cl.[C:13]([C:16]1[CH:17]=[C:18]([CH:29]=[CH:30][CH:31]=1)[CH2:19][N:20]([CH3:28])[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])([OH:15])=O.[NH:32]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[NH:35][CH2:34][C:33]1=[O:42]>CN(C)C1C=CN=CC=1.ClCCl.C(OCC)(=O)C>[N:35]1([C:13]([C:16]2[CH:17]=[C:18]([CH:29]=[CH:30][CH:31]=2)[CH2:19][N:20]([CH3:28])[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:15])[C:36]2[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=2)[NH:32][C:33](=[O:42])[CH2:34]1

Komponenten

7

Edukt 3

HCID 1859492(1H)-Quinoxalinone, 3,4-dihydro-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 224502433-[(Tert-butoxycarbonyl-methyl-amino)-methyl]-benzoic acid

Produkt 1

HCID 69208344tert-butyl N-(3-(1,2,3,4-tetrahydroquinoxalin-3-on-1-carbonyl)benzyl)-N-methylcarbamateAusbeute 27,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

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

Versuchsvorschrift

WSC.HCl (640 mg, 3.4 mmol) and 4-(dimethylamino)pyridine (330 mg, 2.7 mmol) were added to a solution of tert-butyl N-(3-carboxybenzyl)-N-methylcarbamate (700 mg, 2.6 mmol) and 1,2,3,4-tetrahydroquinoxalin-2-one (440 mg, 2.9 mmol) in dichloromethane (20 ml). The mixture was stirred for 18 h, reduced in vacuo and taken up in ethyl acetate. This solution was washed with 0.3N potassium hydrogen sulphate and saturated sodium hydrogen carbonate solutions, dried and reduced. Chromatography (50% EtOAc/50% 60-80 pet.ether) afforded tert-butyl N-(3-(1,2,3,4-tetrahydroquinoxalin-3-on-1-carbonyl) benzyl)-N-methylcarbamate (280 mg, 27%) as an orange oil.

Aufarbeitung

  1. washThis solution was washed with 0.3N potassium hydrogen sulphate and saturated sodium hydrogen carbonate solutions
  2. customdried

Quellen und Nachweise

ORD-Eintrag
ord-8d249a5878c04f61aa1bb2d6f190999f
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07365065B2

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