Triethylamine → [(2-Amino-5-bromo-pyridin-3-ylmethyl)ethoxycarbonylmethyl-amino]acetic acid ethyl ester

HRID 1362056

Reaction equation

HRID 1362056 reaction equation
Br.[Br:2][C:3]1[CH:4]=[C:5]([CH2:10]Br)[C:6]([NH2:9])=[N:7][CH:8]=1.[NH:12]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C(N(CC)CC)C>CC#N>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][N:12]([CH2:10][C:5]1[C:6]([NH2:9])=[N:7][CH:8]=[C:3]([Br:2])[CH:4]=1)[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 80502Diethyl iminodiacetateHCID 534200525-Bromo-3-(bromomethyl)pyridin-2-amine hydrobromide

Product 1

HCID 59456979[(2-Amino-5-bromo-pyridin-3-ylmethyl)ethoxycarbonylmethyl-amino]acetic acid ethyl esterYield 51%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 5-bromo-3-bromomethyl-pyridin-2-ylamine hydrobromide (12.0 g, 34.6 mmol) and diethyl iminodiacetate (7.0 mL, 39.1 mmol) in CH3CN (350 mL) was treated with triethylamine (10.7 mL, 76.1 mmol). After stirring at room temperature under N2 for 4 h, the solvent was removed in vacuo. The resulting yellow slurry was partitioned between H2O (400 mL) and EtOAc (400 mL), and the aqueous layer was extracted with EtOAc (200 mL). The combined organic layers were washed with 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 (6.55 g, 51%) as a light tan oil: MS (ESI) m/e 374 (M+H)+.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe resulting yellow slurry was partitioned between H2O (400 mL) and EtOAc (400 mL)
  3. extractionthe aqueous layer was extracted with EtOAc (200 mL)
  4. washThe combined organic layers were washed with brine (100 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo
  8. customPurification by flash column chromatography (silica gel, CH2Cl2/MeOH, 99:1)

Sources & evidence

ORD record
ord-366cd80ac872488d80edf53025b8836b
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Linked notes

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