Methyl 3-amino-2-methylpropanoate → 3-(4-Methoxy-quinolin-2-ylamino)-2-methyl-propionic acid methyl ester

HRID 2415132Notes

Reaction equation

HRID 2415132 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5](OS(C(F)(F)F)(=O)=O)[CH:4]=1.[CH3:21][O:22][C:23](=[O:28])[CH:24]([CH3:27])[CH2:25][NH2:26]>C(#N)C>[CH3:21][O:22][C:23](=[O:28])[CH:24]([CH3:27])[CH2:25][NH:26][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1

Participants

4

Reactant 2

HCID 10486829Methyl 3-amino-2-methylpropanoateHCID 235256351,1,1-Trifluoromethanesulfonic acid 4-methoxyquinolin-2-yl ester

Product 1

HCID 698371313-(4-Methoxy-quinolin-2-ylamino)-2-methyl-propionic acid methyl esterYield 42%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1,1,1-trifluoromethanesulfonic acid 4-methoxyquinolin-2-yl ester [from Example 1b] (2.03 g, 6.61 mmol) and 3-amino-2-methyl-propionic acid methyl ester (1.5 eq, 1.52 g, 9.91 mmol) in acetonitrile (25 mL) was heated at reflux for five days. It was cooled to room temperature and evaporated to an oil. The crude product was purified via column chromatography on silica (1:1 ethyl acetate/hexane) to give the product (0.75 g, 42%) as an orange oil. [M+H]+ 275.

Workup

  1. temperatureat reflux for five days
  2. customevaporated to an oil
  3. customThe crude product was purified via column chromatography on silica (1:1 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-58ec150cafc145d59574ae66d93d4135
Source dataset
uspto-grants-2004_11
Patent number
US06818655B2

Reaction notes

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