3-Bromo-4-methoxybenzoic acid → HCID 21196391, Verbindung

HRID 1066782Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1066782
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[NH2:35][C:36]1[CH:37]=[N:38][C:39]2[CH2:40][CH2:41][N:42]([CH2:46][C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[CH2:43][C:44]=2[CH:45]=1>CN(C)C=O.ClCCl>[CH2:46]([N:42]1[CH2:41][CH2:40][C:39]2[N:38]=[CH:37][C:36]([NH:35][C:5](=[O:7])[C:4]3[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:2]([Br:1])[CH:3]=3)=[CH:45][C:44]=2[CH2:43]1)[C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1

Komponenten

7

Edukt 4

HCID 668363-Bromo-4-methoxybenzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 108792166-Benzyl-5,6,7,8-tetrahydro-1,6-naphthyridin-3-amine

Produkt 1

HCID 21196391HCID 21196391, VerbindungAusbeute 49,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
2.5 °C

Versuchsvorschrift

3-Bromo-4-methoxybenzoic acid (270 mg; 1.17 mmol) was dissolved in N,N-dimethylformamide (5 ml), the solution was cooled to 0-5° C. and treated with 1-hydroxybenzotriazole(158 mg; 1.17 mmol) then 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (224 mg; 1.17 mmol) and the mixture stirred at 0-5° C. for 0.5 h and treated with a solution of 3-amino-6-benzyl-5,6,7,8-tetrahydro[1,6]naphthyridine (255 mg; 1.06 mmol) in DMF (5 ml). The reaction mixture was stirred at ambient temperature for 72 h then diluted with dichloromethane (100 ml). The resulting mixture was washed with water (5×25 ml), saturated brine, dried (anhydrous magnesium sulfate) and evaporated to dryness in vacuo to yield a mobile, brown oil, which on trituration under 60-80° C. petroleum ether gave a biege powder, which was collected by filtration, washed with 60-80° C. petroleum ether and dried in air. Recrystallisation from ethyl acetate 60-80° C. petroleum ether gave the title compound as a beige powder (236 mg; 49%), m.p. 214-215° C.

Aufarbeitung

  1. washThe resulting mixture was washed with water (5×25 ml), saturated brine
  2. dry with materialdried (anhydrous magnesium sulfate)
  3. customevaporated to dryness in vacuo
  4. customto yield a mobile, brown oil, which on trituration under 60-80° C. petroleum ether
  5. customgave a biege powder, which
  6. filtrationwas collected by filtration
  7. washwashed with 60-80° C. petroleum ether
  8. customdried in air
  9. customRecrystallisation from ethyl acetate 60-80° C. petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-9aec5bf25000451e91f7446aa8d88ae9
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06245778B1

Notizen zur Reaktion

Wird geladen…