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

HRID 1068005Notes

Reaction equation

HRID 1068005 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.[C:49](O)#[C:50][CH2:51][CH2:52][OH:53].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]([CH2:49][C:50]#[C:51][CH2:52][OH:53])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 13931173Butyne-1,4-diolHCID 178522870HCID 178522870, compound

Product 1

HCID 16073878N-[(4-chlorophenyl)methyl]-1-(4-hydroxybut-2-ynyl)-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamideYield 68.7%

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 (393 mg), 1,4-butyne diol (0.45 gm) and diethyl azodicarboxylate (0.18 mL). The mixture is stirred at room temperature overnight, concentrated under reduced pressure and adsorbed onto silica gel. The crude product is purified by flash column chromatography eluting with 2% to 6% methanol in dichloromethane and then by recrystallization from methanol-acetonitrile to afford 0.16 gm of the title compound as a white solid.

Workup

  1. customfrom Preparation No
  2. concentrationconcentrated under reduced pressure
  3. customThe crude product is purified by flash column chromatography
  4. washeluting with 2% to 6% methanol in dichloromethane
  5. customby recrystallization from methanol-acetonitrile

Sources & evidence

ORD record
ord-0b23e5cb114f4624836a2e02a5f615ba
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

Loading…