Triethylamine → [(2-Amino-5-bromo-pyridin-3-ylmethyl)-(2-morpholin-4-yl-ethyl)amino]acetic acid methyl ester

HRID 1362075Notes

Reaction equation

HRID 1362075 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][NH:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.C(N(CC)CC)C.Br.[Br:23][C:24]1[CH:25]=[C:26]([CH2:31]Br)[C:27]([NH2:30])=[N:28][CH:29]=1>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:14])[CH2:4][N:5]([CH2:31][C:26]1[C:27]([NH2:30])=[N:28][CH:29]=[C:24]([Br:23])[CH:25]=1)[CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28583171Methyl 2-{[2-(morpholin-4-yl)ethyl]amino}acetateHCID 534200525-Bromo-3-(bromomethyl)pyridin-2-amine hydrobromide

Product 1

HCID 59456951[(2-Amino-5-bromo-pyridin-3-ylmethyl)-(2-morpholin-4-yl-ethyl)amino]acetic acid methyl esterYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of (2-Morpholin-4-yl-ethylamino)acetic acid methyl ester (0.40 g, 2.0 mmol) and triethylamine (1.0 mL, 7.11 mmol) in DMF (20 mL) was treated with 5-bromo-3-bromomethyl-pyridin-2-ylamine hydrobromide (0.70 g, 2.0 mmol). After stirring at room temperature under for 7 h, the cloudy mixture was diluted with H2O (50 mL) and then extracted with EtOAc (4×50 mL). The combined organic layers were washed with H2O (3×50 mL) and brine (50 mL), dried over Na2SO4, filtered and the solvent was removed in vacuo. Purification by flash column chromatography (silica gel, CH2Cl2/MeOH, 98:2 to 96:4) gave the title compound (0.46 g, 60%) as a colorless oil: MS (ESI) m/e 387 (M+H)+.

Workup

  1. extractionextracted with EtOAc (4×50 mL)
  2. washThe combined organic layers were washed with H2O (3×50 mL) and brine (50 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, 98:2 to 96:4)

Sources & evidence

ORD record
ord-314dec89b3db409e875b24331761f048
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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