Triethylamine → HCID 86711366, compound

HRID 926294Notes

Reaction equation

HRID 926294 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[C:5](/[CH:11]=[CH:12]/[C:13]([O:15][CH3:16])=[O:14])=[N:6][CH:7]=[CH:8][C:9]=1[Cl:10].C(N(CC)CC)C>O1CCOCC1>[Cl:10][C:9]1[C:4]2[CH2:3][CH2:2][NH:1][CH:11]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[C:5]=2[N:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 86711367HCID 86711367, compound

Product 1

HCID 86711366HCID 86711366, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

94-5. A yellow solution of (E)-methyl 3-(3-(2-aminoethyl)-4-chloropyridin-2-yl)acrylate (530 mg, 1.49 mmol) and triethylamine (1.04 mL, 7.47 mmol) in dioxane (10 mL) was stirred at 50° C. for 1 h. The solvent was removed under reduced pressure. The crude product was purified by flash-column chromatography over silicagel (Biotage Isolera One, eluent: gradient from 2% MeOH in DCM to 20% MeOH in DCM in 14 min) to yield the title compound as a clear oil (308 mg). UPLC-MS: MS 241.1 (M+H+); UPLC rt 0.43 min.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe crude product was purified by flash-column chromatography over silicagel (Biotage Isolera One, eluent: gradient from 2% MeOH in DCM to 20% MeOH in DCM in 14 min)

Sources & evidence

ORD record
ord-028541b36bd04802a47c81d6654e7081
Source dataset
uspto-grants-2016_03
Patent number
US09284331B2

Reaction notes

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