Diethylene Glycol → N-[(4-chlorophenyl)methyl]-1-[2-(2-hydroxyethoxy)ethyl]-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamide

HRID 1068001Notes

Reaction equation

HRID 1068001 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]([OH:55])[CH2:50][O:51][CH2:52][CH2:53]O.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]([CH2:53][CH2:52][O:51][CH2:50][CH2:49][OH:55])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8117Diethylene GlycolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178522870HCID 178522870, compound

Product 1

HCID 16073873N-[(4-chlorophenyl)methyl]-1-[2-(2-hydroxyethoxy)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 (165 mg), diethyleneglycol (0.20 mL) and diethyl azodicarboxylate (0.10 mL). The mixture is stirred at room temperature for 2 hrs. The reaction mixture is concentrated under reduced pressure. The crude product is purified by flash column chromatography eluting with 10% to 40% methanol in ethyl acetate and then by recrystallization from ethyl acetate to afford 68 mg of the title compound as a white solid.

Workup

  1. customfrom Preparation No
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. customThe crude product is purified by flash column chromatography
  4. washeluting with 10% to 40% methanol in ethyl acetate
  5. customby recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-d65be07de5e3469691227fbcbe3f52c8
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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