Triphenylphosphine → N-[(4-chlorophenyl)methyl]-1-[2-(2-ethoxyethoxy)ethyl]-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamide

HRID 1068002Notes

Reaction equation

HRID 1068002 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([CH2:21][N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[CH:15][CH:14]=3)=[O:9])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:49]([O:51][CH2:52][CH:53]([O:55][CH2:56][CH3:57])O)[CH3:50].N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:21][N:22]4[CH2:23][CH2:24][O:25][CH2:26][CH2:27]4)[CH:17]=3)[N:12]([CH2:50][CH2:49][O:51][CH2:52][CH2:53][O:55][CH2:56][CH3:57])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11776Triphenylphosphine2×HCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 183240562-Ethoxy-(2-ethoxy)ethanol2×HCID 178522870HCID 178522870, compound

Product 1

HCID 16073874N-[(4-chlorophenyl)methyl]-1-[2-(2-ethoxyethoxy)ethyl]-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A dry flask containing N-(4-chlorobenzyl)-4-hydroxy-6-(4-morpholinylmethyl)-3-quinolinecarboxamide (0.20 gm) from Preparation No. 40 in dry THF (5 mL) under an argon atmosphere is added triphenylphosphine (164 mg), 2-ethoxy-(2-ethoxy)ethanol (0.09 mL) and diethyl azodicarboxylate (0.10 mL). The mixture is stirred at room temperature overnight. The reaction mixture is again treated with triphenylphosphine (164 mg), 2-ethoxy-(2-ethoxy)ethanol (0.09 mL) and diethyl azodicarboxylate (0.10 mL). After 4 hours, the reaction mixture is concentrated under reduced pressure. The crude product is purified by flash column chromatography eluting with acetone and then by recrystallization from ethyl acetate-heptane to afford 0.18 gm of the title compound as a white solid.

Workup

  1. customfrom Preparation No
  2. waitAfter 4 hours
  3. concentrationthe reaction mixture is concentrated under reduced pressure
  4. customThe crude product is purified by flash column chromatography
  5. washeluting with acetone
  6. customby recrystallization from ethyl acetate-heptane

Sources & evidence

ORD record
ord-0ae73ed9cd1b4d8cbcfb8e3cd817d4f1
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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