Triethylamine → Ethyl 2-((2-amino-5-bromopyridin-3-yl)methylamino)acetate
Reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].C(N(CC)CC)C.Br.[Br:17][C:18]1[CH:19]=[C:20]([CH2:25]Br)[C:21]([NH2:24])=[N:22][CH:23]=1>CN(C)C=O>[NH2:24][C:21]1[C:20]([CH2:25][NH:7][CH2:6][C:5]([O:4][CH2:2][CH3:3])=[O:8])=[CH:19][C:18]([Br:17])=[CH:23][N:22]=1Participants
Procedure
Glycine ethyl ester hydrochloride (805 mg, 5.7 mmol) and triethylamine (2.6 mL, 18.46 mmol) were successively added to a solution of 5-bromo-3-(bromomethyl)pyridin-2-amine hydrobromide (2, 5.7 mmol) in dimethylformamide (65 mL) at room temperature. The reaction mixture was stirred overnight then partitioned between ethyl acetate (70 ml) and water (100 mL). The aqueous phase was separated and extracted with ethyl acetate (2×50 mL). The combined organic phases were washed with a saturated solution of sodium chloride (3×40 mL), dried over sodium sulfate, filtered and concentrated to dryness. The residue was purified by chromatography on silica gel, using dichloromethane/methanol (10:0 to 95:5) as eluent. The title product was obtained as a yellow solid (1.1 g, 68%).
Workup
- customthen partitioned between ethyl acetate (70 ml) and water (100 mL)
- customThe aqueous phase was separated
- extractionextracted with ethyl acetate (2×50 mL)
- washThe combined organic phases were washed with a saturated solution of sodium chloride (3×40 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated to dryness
- customThe residue was purified by chromatography on silica gel
Sources & evidence
- ORD record
- ord-8af2f4265a024dfe91b0b2dbcf96388c
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846711B2
Reaction notes
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