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 901604Notes

Reaction equation

HRID 901604 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 20° 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-97c8277e409f49f5a7b4c2a9ee9f827e
Source dataset
uspto-grants-2008_04
Patent number
US07361787B2

Reaction notes

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