2-Chloro-5-nitropyridine → HCID 60209557, compound

HRID 2246206Notes

Reaction equation

HRID 2246206 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.Cl.[N:12]1([C:18]([O:20][CH2:21][C:22]([NH:24][CH3:25])=[O:23])=[O:19])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(N(CC)C(C)C)(C)C>ClCCCl>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:15]2[CH2:14][CH2:13][N:12]([C:18]([O:20][CH2:21][C:22]([NH:24][CH3:25])=[O:23])=[O:19])[CH2:17][CH2:16]2)=[N:3][CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 783082-Chloro-5-nitropyridineHCID 81531DiisopropylethylamineHCID 60209555HCID 60209555, compound

Product 1

HCID 60209557HCID 60209557, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

1.84 g (11.6 mmol) of 2-chloro-5-nitropyridine are added to a solution of 2.05 g (8.62 mmol) of 2-(methylamino)-2-oxoethyl 1-piperazinecarboxylate hydrochloride, obtained in step 5.2., and 3.85 ml (22.4 mmol) of N,N diisopropylethylamine in 55 ml of 1,2-dichloroethane. This reaction mixture is maintained at 70° C. for 5 hours. The mixture is allowed to cool to room temperature and concentrated under reduced pressure, and the residue thus obtained is purified by chromatography on silica gel, eluting with a 98/2 mixture of dichloromethane and methanol. 2.48 g of product are obtained in the form of a pale yellow solid, and are used without further purification in the following step.

Workup

  1. customobtained in step 5.2
  2. temperatureto cool to room temperature
  3. concentrationconcentrated under reduced pressure
  4. customthe residue thus obtained
  5. customis purified by chromatography on silica gel
  6. washeluting with a 98/2 mixture of dichloromethane and methanol

Sources & evidence

ORD record
ord-2a969cdefd6a409cb4775bf800b6eadc
Source dataset
uspto-grants-2010_03
Patent number
US07687503B2

Reaction notes

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