Diethyl Ether → {2-[2-(2-[Bis{4-methoxybenzyl}amino]-6-chloro-5-methyl-3-nitropyridin-4-ylamino)ethoxy]ethyl}carbamic acid tert-butyl ester

HRID 1008098Notes

Reaction equation

HRID 1008098 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][NH:14][C:15]1[C:20]([CH3:21])=[C:19]([Cl:22])[N:18]=[C:17](OS(C(F)(F)F)(=O)=O)[C:16]=1[N+:31]([O-:33])=[O:32])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:34][O:35][C:36]1[CH:52]=[CH:51][C:39]([CH2:40][NH:41][CH2:42][C:43]2[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][CH:44]=2)=[CH:38][CH:37]=1.C(N(CC)CC)C.C(OCC)C>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][NH:14][C:15]1[C:20]([CH3:21])=[C:19]([Cl:22])[N:18]=[C:17]([N:41]([CH2:40][C:39]2[CH:38]=[CH:37][C:36]([O:35][CH3:34])=[CH:52][CH:51]=2)[CH2:42][C:43]2[CH:44]=[CH:45][C:46]([O:49][CH3:50])=[CH:47][CH:48]=2)[C:16]=1[N+:31]([O-:33])=[O:32])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 714952Bis(4-methoxybenzyl)amineHCID 86590767Trifluoromethanesulfonic acid 4-[(2-{2-[(tert-butoxycarbonyl)amino]ethoxy}ethyl)amino]-6-chloro-5-methyl-3-nitropyridin-2-yl ester

Product 1

HCID 86590766{2-[2-(2-[Bis{4-methoxybenzyl}amino]-6-chloro-5-methyl-3-nitropyridin-4-ylamino)ethoxy]ethyl}carbamic acid tert-butyl esterYield 50.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of trifluoromethanesulfonic acid 4-[(2-{2-[(tert-butoxycarbonyl)amino]ethoxy}ethyl)amino]-6-chloro-5-methyl-3-nitropyridin-2-yl ester (14.3 g, 27.4 mmol), bis(4-methoxybenzyl)amine (7.00 g, 27.4 mmol), and triethylamine (3.82 mL, 27.4 mmol) in toluene (250 mL) was heated at 90° C. for two hours and then allowed to cool to room temperature overnight. Diethyl ether (300 mL) was added, and the solution was washed with water (200 mL) and brine (200 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified twice by column chromatography on silica gel (eluting sequentially with 80:20 hexanes:ethyl acetate and 70:30 hexanes:ethyl acetate) to provide 8.73 g of {2-[2-(2-[bis{4-methoxybenzyl}amino]-6-chloro-5-methyl-3-nitropyridin-4-ylamino)ethoxy]ethyl}carbamic acid tert-butyl ester.

Workup

  1. washthe solution was washed with water (200 mL) and brine (200 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified twice by column chromatography on silica gel (
  6. washeluting sequentially with 80:20 hexanes

Sources & evidence

ORD record
ord-e566ce98209e40b6bb959d4c83691072
Source dataset
uspto-grants-2004_09
Patent number
US06797718B2

Reaction notes

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