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

HRID 469212Notes

Reaction equation

HRID 469212 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>[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

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-e2549d7d4aac4e1d9617f29d65c942b3
Source dataset
uspto-grants-2014_01
Patent number
US08629126B2

Reaction notes

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