Acetic Acid → HCID 67172438, compound

HRID 1891273Notes

Reaction equation

HRID 1891273 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][NH:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:6][CH:7]=1.O.[O-:17][C:18]#[N:19].[K+].C(O)(=O)C>O1CCOCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:18]([NH2:19])=[O:17])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 11378442Potassium cyanateHCID 64124842HCID 64124842, compound

Product 1

HCID 67172438HCID 67172438, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Ethyl 2-((5-bromopyridin-2-yl)methylamino)acetate (9J1) (41.6 mmol, 11.37 g) was dissolved in dioxane (80 ml) and water (80 ml) and potassium cyanate (62.4 mmol, 5.07 g) added. After 10 min, acetic acid (133 mmol, 8.00 g) was added and the reaction mixture stirred at room temperature under nitrogen overnight. The reaction mixture was quenched with saturated sodium bicarbonate (to pH 8-9) and then extracted with dichloromethane (3×). The organic layers were combined, washed with water, brine and dried using a hydrophobic frit, then concentrated under reduced pressure to give ethyl 2-(1-((5-bromopyridin-2-yl)methyl)ureido)acetate (9J2) 11.08 g (84%) which was used without further purification. 1H NMR (400 MHz, CDCl3) 8.61 (d, 1H) 7.84 (dd 1H) 7.39 (d, 1H) 5.35 (bs, 2H) 4.51 (s, 2H) 4.17 (q, 2H) 4.11 (s, 2H) 1.25 (t, 3H)

Workup

  1. customThe reaction mixture was quenched with saturated sodium bicarbonate (to pH 8-9)
  2. extractionextracted with dichloromethane (3×)
  3. washwashed with water, brine
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5523ba4a65dd401cb49c9e52ecf395a7
Source dataset
uspto-grants-2013_08
Patent number
US08507521B2

Reaction notes

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