Water → HCID 15661730, compound

HRID 977574Notes

Reaction equation

HRID 977574 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-c9efc7038330417188a84622f37677fd
Source dataset
uspto-grants-1997_03
Patent number
US05614634

Reaction notes

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