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

HRID 1094171Notes

Reaction equation

HRID 1094171 reaction equation
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>[CH2:36]([O:35][P:31]([CH2:30][CH:29]([NH:2][CH2:3][C:4]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][C:9]([NH:16][CH:17]3[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]3)=[C:10]([F:15])[CH:11]=2)[N:6]([CH:23]([CH2:26][CH3:27])[CH2:24][CH3:25])[CH:5]=1)[CH3:39])(=[O:38])[O:32][CH2:33][CH3:34])[CH3:37]

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-6d44964fb79643ab98fbb321adf2431b
Source dataset
uspto-grants-2012_03
Patent number
US08133882B2

Reaction notes

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