Triethylamine → N-[(6-bromopyridin-2-yl)methyl]-2-cyanoacetamide

HRID 385892Notes

Reaction equation

HRID 385892 reaction equation
Cl.[Br:2][C:3]1[N:8]=[C:7]([CH2:9][NH2:10])[CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:18]([CH2:20][C:21](O)=[O:22])#[N:19].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1>CN(C=O)C.C(OCC)(=O)C>[Br:2][C:3]1[N:8]=[C:7]([CH2:9][NH:10][C:21](=[O:22])[CH2:20][C:18]#[N:19])[CH:6]=[CH:5][CH:4]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 9740Cyanoacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 457898861-(6-Bromopyridin-2-yl)methanamine--hydrogen chloride (1/1)

Product 1

HCID 59526353N-[(6-bromopyridin-2-yl)methyl]-2-cyanoacetamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-Bromo-2-pyridinemethanamine hydrochloride (0.25 g, 1.12 mmol) was taken up in DMF (8.4 mL) and triethylamine (0.31 mL, 2.24 mmol) was added. After five minutes, cyanoacetic acid (0.095 g, 1.12 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.21 g, 1.12 mmol), 1-hydroxybenzotriazole hydrate (0.18 g, 1.14 mmol) were added and the reaction was maintained at room temperature overnight. Upon completion the mixture was diluted with ethyl acetate, washed with water, dried over magnesium sulfate, filtered and concentrated. The crude material was purified by silica gel chromatography to yield the title compound.

Workup

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-d9570feb955744e3a5b2f02a1eb1a374
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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