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 503065Notes

Reaction equation

HRID 503065 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-5c05ede074de439d8c3825e2ae4ac29f
Source dataset
uspto-grants-2010_08
Patent number
US07776895B2

Reaction notes

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