Water → Methyl 2-(((2-amino-5-bromopyridin-3-yl)methyl)(4-methoxybenzyl)amino)acetate

HRID 83009Notes

Reaction equation

HRID 83009 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][NH:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:5][CH:4]=1.C(N(CC)CC)C.Br.[Br:24][C:25]1[CH:26]=[C:27]([CH2:32]Br)[C:28]([NH2:31])=[N:29][CH:30]=1.O>CN(C=O)C.C(OCC)(=O)C>[NH2:31][C:28]1[C:27]([CH2:32][N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:15][CH:14]=2)[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:26][C:25]([Br:24])=[CH:30][N:29]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10846084N-((4-Methoxyphenyl)methyl)glycine methyl esterHCID 534200525-Bromo-3-(bromomethyl)pyridin-2-amine hydrobromide

Product 1

HCID 67154556Methyl 2-(((2-amino-5-bromopyridin-3-yl)methyl)(4-methoxybenzyl)amino)acetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 2-(4-methoxybenzylamino)acetate (760 mg, 3.63 mmol) and triethylamine (840 μL, 6.60 mmol) were successively added to a solution of 5-bromo-3-(bromomethyl)pyridine-2-amine hydrobromide (1.0 g, 3.30 mmol) in DMF (17 mL) at room temperature. The reaction mixture was stirred for 8 hours then diluted by addition of water (50 mL) and ethyl acetate (50 mL). The aqueous phase was separated and extracted with ethyl actetate (3×50 mL). The combined organic phases were washed with a saturated solution of sodium chloride (3×50 mL), dried over sodium sulphate, filtered and concentrated to dryness. The title compound was obtained as an orange oil (1.05 g, 93%) which was used in the next step without further purification.

Workup

  1. customThe aqueous phase was separated
  2. extractionextracted with ethyl actetate (3×50 mL)
  3. washThe combined organic phases were washed with a saturated solution of sodium chloride (3×50 mL)
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-355ad432c06348d082c3b944eafb9ba6
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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