Triethylamine → 4-[(3-Nitro[1,5]naphthyridin-4-ylamino)methyl]tetrahydropyran-4-ol

HRID 44752

Reaktionsgleichung

Reaktionsgleichung von HRID 44752
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].C(N(CC)CC)C.[NH2:22][CH2:23][C:24]1([OH:30])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>ClCCl>[N+:12]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[NH:22][CH2:23][C:24]1([OH:30])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)=[N:10][CH:9]=[CH:8][CH:7]=2)([O-:14])=[O:13]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 131227874-Chloro-3-nitro-1,5-naphthyridineHCID 436087544-(Aminomethyl)oxan-4-ol

Produkt 1

HCID 669191374-[(3-Nitro[1,5]naphthyridin-4-ylamino)methyl]tetrahydropyran-4-olAusbeute 93,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 4-chloro-3-nitro[1,5]naphthyridine (16.6 g, 79.0 mmol) in dichloromethane (250 mL) and triethylamine (14.3 mL, 102.7 mmol) was cooled to 4° C. A solution of 4-aminomethyltetrahydropyran-4-ol (11.4 g, 86.9 mmol) in dichloromethane (70 mL) was added dropwise over a period of 30 minutes. The reaction mixture was allowed to stir at ambient temperature over the weekend and then it was concentrated under reduced pressure. The residue was stirred with water (300 mL). The resulting solid was isolated by filtration, rinsed with water, and dried in a vacuum oven at 50° C. for 4 hours to provide 22.53 g of 4-[(3-nitro[1,5]naphthyridin-4-ylamino)methyl]tetrahydropyran-4-ol.

Aufarbeitung

  1. concentrationit was concentrated under reduced pressure
  2. stirringThe residue was stirred with water (300 mL)
  3. customThe resulting solid was isolated by filtration
  4. washrinsed with water
  5. customdried in a vacuum oven at 50° C. for 4 hours

Quellen und Nachweise

ORD-Eintrag
ord-b13aac86498640cbb8957bf3bf6a0172
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541438B2

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