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

HRID 1068003Notes

Reaction equation

HRID 1068003 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([CH:51](O)[CH2:52][S:53][CH2:54][CH:55](O)CC)C.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]([CH2:51][CH2:52][S:53][CH2:54][CH3:55])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 548436Sulfide, bis(2-hydroxybutyl)HCID 178522870HCID 178522870, compound

Product 1

HCID 16073876N-[(4-chlorophenyl)methyl]-1-(2-ethylsulfanylethyl)-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 (393 mg), ethyl 2-hydroxyethylsulfide (0.16 mL) and diethyl azodicarboxylate (0.18 mL). The mixture is stirred at room temperature overnight then concentrated under reduced pressure. The crude product is purified by flash column chromatography eluting with 2% to 6% methanol in dichloromethane and then by recrystallization from ethanolcyclohexane to afford 0.21 gm of the title compound as a white solid.

Workup

  1. customfrom Preparation No
  2. concentrationthen concentrated 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 ethanolcyclohexane

Sources & evidence

ORD record
ord-94118e7b87a449688e80c0a1c478192c
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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