3-Pyridinecarbonyl chloride, hydrochloride (1:1) → N-{3-[({[3-({2-({6-[(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)ethoxy}methyl)phenyl]amino}carbonyl)amino]-phenyl}pyridine-3-carboxamide

HRID 2116962Notes

Reaction equation

HRID 2116962 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][N:29]3[CH2:33][C@@H:32]([C:34]4[CH:45]=[CH:44][C:37]5[O:38][C:39]([CH3:43])([CH3:42])[O:40][CH2:41][C:36]=5[CH:35]=4)[O:31][C:30]3=[O:46])[CH:13]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.Cl.[C:48](Cl)(=[O:55])[C:49]1[CH:54]=[CH:53][CH:52]=[N:51][CH:50]=1.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[CH3:43][C:39]1([CH3:42])[O:38][C:37]2[CH:44]=[CH:45][C:34]([C@H:32]3[O:31][C:30](=[O:46])[N:29]([CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][O:22][CH2:21][CH2:20][O:19][CH2:18][C:14]4[CH:13]=[C:12]([NH:11][C:9]([NH:8][C:4]5[CH:3]=[C:2]([NH:1][C:48]([C:49]6[CH:50]=[N:51][CH:52]=[CH:53][CH:54]=6)=[O:55])[CH:7]=[CH:6][CH:5]=5)=[O:10])[CH:17]=[CH:16][CH:15]=4)[CH2:33]3)=[CH:35][C:36]=2[CH2:41][O:40]1

Participants

5

Reactant 3

HCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 66845582N-(3-Aminophenyl)-N'-[3-({2-({6-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)ethoxy}methyl)phenyl]urea

Product 1

HCID 66845055N-{3-[({[3-({2-({6-[(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)ethoxy}methyl)phenyl]amino}carbonyl)amino]-phenyl}pyridine-3-carboxamideYield 89.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of N-(3-aminophenyl)-N′-[3-({2-({6-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)ethoxy}methyl)phenyl]-urea (0.20 g) in pyridine (4 ml) was treated under nitrogen at 200 with nicotinoyl chloride hydrochloride (0.118 g) and the mixture stirred for 5.5 h. Sat. sodium bicarbonate solution (25 ml) was added and the product was extracted with dichloromethane (3×20 ml). The combined organic layer was dried (Na2SO4) and the solvent removed in vacuo to give a residue that was purified by SPE. Elution with dichloromethane-EtOAc (1:0, 1:1, then 0:1), then MeOH-EtOAc (1:50), followed by solvent evaporation in vacuo gave the title compound (0.209 g). LCMS RT=3.54 min, ES+ve 738 (MH)+.

Workup

  1. extractionthe product was extracted with dichloromethane (3×20 ml)
  2. dry with materialThe combined organic layer was dried (Na2SO4)
  3. customthe solvent removed in vacuo
  4. customto give a residue that
  5. customwas purified by SPE
  6. washElution with dichloromethane-EtOAc (1:0, 1:1
  7. custom0:1), then MeOH-EtOAc (1:50), followed by solvent evaporation in vacuo

Sources & evidence

ORD record
ord-ac0ed6440aa84a6f8529d66eb6a14901
Source dataset
uspto-grants-2008_10
Patent number
US07439393B2

Reaction notes

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