Triethylamine → Diethyl [2-({[7-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]methyl}amino)propyl]phosphonate

HRID 469212Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 469212
Cl.[NH2:2][CH2:3][C:4]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][C:9]([NH:16][CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)=[C:10]([F:15])[CH:11]=2)[N:6]([CH:23]([CH2:26][CH3:27])[CH2:24][CH3:25])[CH:5]=1.O=[C:29]([CH3:39])[CH2:30][P:31](=[O:38])([O:35][CH2:36][CH3:37])[O:32][CH2:33][CH3:34].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(N(CC)CC)C>C1COCC1.O.C(O)(=O)C>[CH:17]1([NH:16][C:9]2[CH:8]=[C:7]3[C:12]([C:13](=[O:14])[C:4]([CH2:3][NH:2][CH:29]([CH3:39])[CH2:30][P:31](=[O:38])([O:35][CH2:36][CH3:37])[O:32][CH2:33][CH3:34])=[CH:5][N:6]3[CH:23]([CH2:26][CH3:27])[CH2:24][CH3:25])=[CH:11][C:10]=2[F:15])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 140281-Diethoxyphosphorylpropan-2-oneHCID 5049666Sodium triacetoxyborohydrideHCID 666368533-(aminomethyl)-7-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoroquinolin-4(1H)-one hydrochloride

Produkt 1

HCID 86633052Diethyl [2-({[7-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]methyl}amino)propyl]phosphonate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

250 mg of 3-(aminomethyl)-7-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoroquinolin-4(1H)-one hydrochloride was dissolved in 25 ml of THF, and 0.11 ml of diethyl (2-oxopropyl)phosphonate and 123 mg of sodium triacetoxyborohydride, 0.16 ml of triethylamine and 1.25 ml of acetic acid were added in that order, followed by overnight stirring at room temperature. Water was added, and the insoluble materials were collected by filtration and then purified by silica gel column chromatography to obtain 135 mg of diethyl [2-({[7-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]methyl}amino)propyl]phosphonate.

Aufarbeitung

  1. filtrationthe insoluble materials were collected by filtration
  2. custompurified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e2549d7d4aac4e1d9617f29d65c942b3
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629126B2

Notizen zur Reaktion

Wird geladen…