Triethylamine → HCID 61699828, compound

HRID 1401159Notes

Reaction equation

HRID 1401159 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[NH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].C(N(CC)CC)C>C(#N)C>[Cl:8][C:4]1[N:3]=[C:2]([NH:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]=[N:6][CH:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12176Glycine ethyl esterHCID 785042,6-Dichloropyrazine

Product 1

HCID 61699828HCID 61699828, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To 2,6-dichloropyrazine (50 g, 336 mmol) and ethyl 2-aminoacetate (34.6 g, 336 mmol) was added triethylamine (140 mL, 1007 mmol) and acetonitrile (350 mL). The reaction was heated at 80° C. for 3 d. Precipitated triethylamine salts were removed by filtration and washed with ethyl acetate and hexane (1:1) multiple times. The filtrate and wash solvent were combined and concentrated. The resulting white-yellow precipitate was filtered and washed with 20% ethyl acetate in hexane to afford an off-white solid. The filtrate was subjected to the same process to give an additional batch of off-yellow solid. The batches were combined to afford the title compound (35.5 g, 164 mmol, 49% yield). MS (ESI) m/z 216.1 [M+1]+.

Workup

  1. customPrecipitated triethylamine salts were removed by filtration
  2. washwashed with ethyl acetate and hexane (1:1) multiple times
  3. washThe filtrate and wash solvent
  4. concentrationconcentrated
  5. filtrationThe resulting white-yellow precipitate was filtered
  6. washwashed with 20% ethyl acetate in hexane
  7. customto afford an off-white solid
  8. customto give an additional batch of off-yellow solid

Sources & evidence

ORD record
ord-c0d3146dfb854342a79c32bc52621084
Source dataset
uspto-grants-2014_12
Patent number
US08907087B2

Reaction notes

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