1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 3-[4-(3-Bromo-phenylamino)-quinazolin-7-ylcarbamoyl]acrylic acid ethyl ester

HRID 507447Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 507447
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=3)=[N:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[C:20]([O:27][CH2:28][CH3:29])(=[O:26])/[CH:21]=[CH:22]/[C:23]([O-])=[O:24].Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[CH2:28]([O:27][C:20](=[O:26])[CH:21]=[CH:22][C:23](=[O:24])[NH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=3)=[N:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1)[CH3:29]

Komponenten

5

Edukt 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 53280457-Amino-4-[(3-bromophenyl)amino]quinazoline2×HCID 58782252-Butenedioic acid, monoethyl ester

Produkt 1

HCID 537015123-[4-(3-Bromo-phenylamino)-quinazolin-7-ylcarbamoyl]acrylic acid ethyl esterAusbeute 23,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

To an ice cold solution of 0.158 g of 7-amino-4-(3-bromoanilino)-quinazoline and 0.216 g of monoethyl fumarate in 3 mL of dry dimethylformamide was added 0.288 g of 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide HCl (EDAC). 7-Amino-4-(3-bromoanilino)-quinazoline can be made by methods well-known to those skilled in the art. See, for example, J Med Chem, 1995:3482, which is hereby incorporated by reference. After stirring at 5° C. for 5 minutes, the ice bath was removed, and the reaction was permitted to warm to room temperature where it stirred for 15 hours. The reaction was poured into cold water, and the suspension was made basic with the addition of a saturated sodium bicarbonate solution. The resulting solid was collected by filtration, washed with water, and then recrystallized from 50 mL of ethanol to afford 0.052 g of the desired product, mp >260° C.

Aufarbeitung

  1. customthe ice bath was removed
  2. temperatureto warm to room temperature where it
  3. stirringstirred for 15 hours
  4. additionThe reaction was poured into cold water
  5. additionthe suspension was made basic with the addition of a saturated sodium bicarbonate solution
  6. filtrationThe resulting solid was collected by filtration
  7. washwashed with water
  8. customrecrystallized from 50 mL of ethanol

Quellen und Nachweise

ORD-Eintrag
ord-8507c21bdb4a4dc694ecbd0cf5fc59b5
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786131B2

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