Triethylamine → HCID 59332883, compound

HRID 1879994Notes

Reaction equation

HRID 1879994 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.[CH2:13]([O:15][C:16](=[O:20])[C@H:17]([CH3:19])[NH2:18])[CH3:14].C(N(CC)CC)C>CN(C=O)C>[NH2:9][C:6]1[C:5]([CH2:10][NH:18][C@@H:17]([CH3:19])[C:16]([O:15][CH2:13][CH3:14])=[O:20])=[CH:4][C:3]([Br:2])=[CH:8][N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2724356L-Alanine, ethyl ester, hydrochloride (1:1)HCID 534200525-Bromo-3-(bromomethyl)pyridin-2-amine hydrobromide

Product 1

HCID 59332883HCID 59332883, compoundYield 25%

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) is added L-alanine ethyl 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 was quenched with water (20 mL) and the product extracted with ethyl acetate (4×20 mL), the combined organic layers are dried over sodium sulfate and concentrated. The crude reaction mixture is purified using preparative HPLC to give the final product as a white solid (530 mg, 25%): 1H NMR (300 MHz, DMSO-d6) δ 7.91 (s, 1H), 7.47 (s, 1H), 6.20 (b, 1H), 4.15-4.07 (m, 2H), 3.49 (b, 2H), 3.27 (m, 1H), 3.34 (s, 2H), 1.17-1.24 (m, 6H).

Workup

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

Sources & evidence

ORD record
ord-e2cc59244c834589947d63c2064a0f2a
Source dataset
uspto-grants-2012_11
Patent number
US08318720B2

Reaction notes

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