Triethylamine → HCID 59332858, compound

HRID 1879996Notes

Reaction equation

HRID 1879996 reaction equation
Br.[Br:2][C:3]1[CH:4]=[C:5]([CH2:10]Br)[C:6]([NH2:9])=[N:7][CH:8]=1.Cl.[CH3:13][O:14][C:15](=[O:19])[C@@H:16]([CH3:18])[NH2:17].C(N(CC)CC)C>CN(C=O)C>[NH2:9][C:6]1[C:5]([CH2:10][NH:17][C@H:16]([CH3:18])[C:15]([O:14][CH3:13])=[O:19])=[CH:4][C:3]([Br:2])=[CH:8][N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11182647Methyl D-alaninate hydrochlorideHCID 534200525-Bromo-3-(bromomethyl)pyridin-2-amine hydrobromide

Product 1

HCID 59332858HCID 59332858, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-bromo-3-(bromomethyl)pyridin-2-amine hydrobromide (2.5 g, 7.3 mmol) in DMF (10 mL) was added D-alanine methyl ester hydrochloride (1.67 g, 10.9 mmol) and triethylamine (5 mL, 36 mmol) and the reaction was stirred at room temperature overnight. The reaction is quenched with water (20 mL) and the product was extracted with ethyl acetate (4×20 mL), the combined organic layers dried over sodium sulfate and concentrated. The crude reaction mixture was purified using a silica gel column eluting with ethyl acetate to give the final product as a white solid (1 g, 50%): 1H NMR (400 MHz, CDCl3) δ 8.03 (s, 1H), 7.35 (s, 1H), 5.54 (bs, 2H), 3.73 (d, 1H, J=13.2 Hz), 3.54 (d, 1H, J=13.2 Hz), 3.36-3.34 (m, 1H), 2.96 (s, 3H), 1.35 (d, 3H, J=6.8 Hz).

Workup

  1. customThe reaction is quenched with water (20 mL)
  2. extractionthe product was extracted with ethyl acetate (4×20 mL)
  3. dry with materialthe combined organic layers dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude reaction mixture
  6. customwas purified
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-8a8113f13efc4c61baaac7c7d8f5203e
Source dataset
uspto-grants-2012_11
Patent number
US08318720B2

Reaction notes

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