Methanol → 4-(3-Acetyl-5-ethoxy-2-methyl-1,4-dihydro-1,6-naphthyridin-4-yl)-1-naphthonitrile

HRID 1951421

Reaktionsgleichung

Reaktionsgleichung von HRID 1951421
[C:1]([C:4]1[CH:13]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([C:24]#[N:25])=[CH:16][CH:15]=2)[C:12]2[C:11](=[O:26])[NH:10][CH:9]=[CH:8][C:7]=2[NH:6][C:5]=1[CH3:27])(=[O:3])[CH3:2].ClCCl.F[B-](F)(F)F.[CH2:36]([O+](CC)CC)[CH3:37].CO>O>[C:1]([C:4]1[CH:13]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([C:24]#[N:25])=[CH:16][CH:15]=2)[C:12]2[C:7](=[CH:8][CH:9]=[N:10][C:11]=2[O:26][CH2:36][CH3:37])[NH:6][C:5]=1[CH3:27])(=[O:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 6344DichloromethaneHCID 2723982Triethyloxonium tetrafluoroborateHCID 596030254-(3-Acetyl-2-methyl-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridin-4-yl)-1-naphthonitrile

Produkt 1

HCID 236279894-(3-Acetyl-5-ethoxy-2-methyl-1,4-dihydro-1,6-naphthyridin-4-yl)-1-naphthonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

93 mg (0.262 mmol) of 4-(3-acetyl-2-methyl-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridin-4-yl)-1-naphthonitrile are dissolved under an argon atmosphere in 5 ml of abs. dichloromethane, and 99.4 mg (0.268 mmol) of triethyloxonium tetrafluoroborate are added. After a reaction time of two hours at room temperature (reaction checked by HPLC), the mixture is mixed with 5 ml of methanol and 0.5 ml of water and again stirred for 2 h. It is then diluted with 20 ml of water and extracted three times with dichloromethane. The combined organic phases are dried with sodium sulfate, and the solvent is removed in a rotary evaporator. The residue is purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80→95:5). 60 mg (59.8% of theory) of the title compound are obtained.

Aufarbeitung

  1. customAfter a reaction time of two hours at room temperature (reaction checked by HPLC)
  2. extractionextracted three times with dichloromethane
  3. dry with materialThe combined organic phases are dried with sodium sulfate
  4. customthe solvent is removed in a rotary evaporator
  5. customThe residue is purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80→95:5)

Quellen und Nachweise

ORD-Eintrag
ord-fe52c5d155c844f0a03dcff3b06b4614
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08404709B2

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