Triethylamine → 2-[(2-Amino-5-bromo-pyridin-3-ylmethyl)amino]-2-methylpropionic acid methyl ester

HRID 1362118Notes

Reaction equation

HRID 1362118 reaction equation
Br.[Br:2][C:3]1[CH:4]=[C:5]([CH2:10]Br)[C:6]([NH2:9])=[N:7][CH:8]=1.[CH3:12][O:13][C:14](=[O:19])[C:15]([NH2:18])([CH3:17])[CH3:16].C(N(CC)CC)C>CN(C=O)C.O>[CH3:12][O:13][C:14](=[O:19])[C:15]([NH:18][CH2:10][C:5]1[C:6]([NH2:9])=[N:7][CH:8]=[C:3]([Br:2])[CH:4]=1)([CH3:17])[CH3:16]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 4186341Methyl 2-amino-2-methylpropanoateHCID 534200525-Bromo-3-(bromomethyl)pyridin-2-amine hydrobromide

Product 1

HCID 594569402-[(2-Amino-5-bromo-pyridin-3-ylmethyl)amino]-2-methylpropionic acid methyl esterYield 40.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 5-bromo-3-bromomethyl-pyridin-2-ylamine hydrobromide (11.0 g, 31.7 mmol) and 2-amino-2-methyl-propionic acid methyl ester (5.80 g, 49.5 mmol) in DMF (220 mL) was treated with triethylamine (9.0 mL, 18.5 mmol). After stirring at room temperature for 3 d, the mixture was diluted with H2O (400 mL) and then extracted with EtOAc (4×200 mL). The combined organic layers were washed with H2O (3×100 mL) and brine (100 mL), dried over Na2SO4, filtered and the solvent was removed in vacuo. Purification by flash column chromatography (silica gel, CH2Cl2/MeOH, 99:1) gave the title compound (3.87 g, 40%) as a light yellow solid: MS (ESI) m/e 302 (M+H)+.

Workup

  1. extractionextracted with EtOAc (4×200 mL)
  2. washThe combined organic layers were washed with H2O (3×100 mL) and brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo
  6. customPurification by flash column chromatography (silica gel, CH2Cl2/MeOH, 99:1)

Sources & evidence

ORD record
ord-b62571daaee847f691cea81b3090fc31
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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