Ethyl bromopyruvate → HCID 11514651, compound

HRID 1371569Notes

Reaction equation

HRID 1371569 reaction equation
[NH2:1][C:2]1[C:3]([C:7]([NH:9][CH2:10][CH:11]([CH3:13])[CH3:12])=[NH:8])=[N:4][O:5][N:6]=1.Br[CH2:15][C:16](=O)[C:17]([O:19][CH2:20][CH3:21])=[O:18].C(=O)(O)[O-].[Na+]>CC(O)C>[NH2:1][C:2]1[C:3]([C:7]2[N:9]([CH2:10][CH:11]([CH3:13])[CH3:12])[CH:15]=[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:8]=2)=[N:4][O:5][N:6]=1

Participants

5

Reactant 3

HCID 66144Ethyl bromopyruvateHCID 516892Sodium BicarbonateHCID 178449179HCID 178449179, compound

Product 1

HCID 11514651HCID 11514651, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-amino-N-isobutyl-1,2,5-oxadiazole-3-carboxamidine (18 mg, 0.1 mmol), ethyl bromopyruvate (28 μL, 0.2 mmol) and sodium bicarbonate (17 mg, 0.2 mmol) in iPrOH (1 mL) was microwaved for 20 minutes at 150° C. Crude reaction mixture was purified via preparative HPLC to afford the title compound as a white solid. MS 280.2 as M+1 peak. HPLC Method B Rt 3.5 min. 1HNMR (CDCl3) 7.65 (s, 1H); 5.65 (s, 2H); 5.32 (q, 2H); 4.2 (d, 2H); 2.1 (m, 1H); 1.35 (t, 3H); 0.91 (d, 6H).

Workup

  1. customwas microwaved for 20 minutes at 150° C
  2. customCrude reaction mixture
  3. customwas purified via preparative HPLC

Sources & evidence

ORD record
ord-fd7c396593394741a234140311a2e288
Source dataset
uspto-grants-2007_01
Patent number
US07157476B2

Reaction notes

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