Water → HCID 15661730, compound

HRID 1756329Notes

Reaction equation

HRID 1756329 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.C(N(CC)CC)C.[Cl-].[CH3:17][O:18][C:19](=[O:26])[CH2:20][CH2:21][CH2:22][C:23](O)=[O:24].O>O1CCCC1.C(OCC)C>[CH3:17][O:18][C:19](=[O:26])[CH2:20][CH2:21][CH2:22][C:23]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1)=[O:24]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 3008092-Amino-6-bromopyridineHCID 53445129Glutaric acid monomethylester chloride

Product 1

HCID 15661730HCID 15661730, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.0 g of 2-amino-6-bromopyridine and 580 mg of triethylamine in 12 ml of tetrahydrofuran is mixed with stirring and ice cooling by instillation with 0.78 ml of glutaric acid methyl ester chloride and the mixture is stirred for 17 hours at room temperature. The reaction mixture is added to water, shaken out with diethyl ether, the organic phase is dried (sodium sulfate) and concentrated by evaporation. The residue is chromatographed on silica gel with dichloromethane/methanol=95/5. 668 mg of 5-(6-bromo-2-pyridylamino)-5-oxo-pentanoic acid methyl ester of melting point 128°-131° C. is obtained.

Workup

  1. dry with materialthe organic phase is dried (sodium sulfate)
  2. concentrationconcentrated by evaporation
  3. customThe residue is chromatographed on silica gel with dichloromethane/methanol=95/5

Sources & evidence

ORD record
ord-aa597979a1074e0784e5892e1f32608c
Source dataset
uspto-grants-1995_08
Patent number
US05440044

Reaction notes

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