N,N'-Dimethylethylenediamine → HCID 22036355, compound

HRID 493351Notes

Reaction equation

HRID 493351 reaction equation
Cl[C:2]1[C:7]([O:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:6][CH:5]=[CH:4][N:3]=1.[CH3:18][NH:19][CH2:20][CH2:21][NH:22][CH3:23]>>[CH3:18][N:19]([C:2]1[C:7]([O:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:6][CH:5]=[CH:4][N:3]=1)[CH2:20][CH2:21][NH:22][CH3:23]

Participants

3

Reactant 2

HCID 8070N,N'-DimethylethylenediamineHCID 22036365HCID 22036365, compound

Product 1

HCID 22036355HCID 22036355, compound

Procedure

A mixture of 2-chloro-3-(2-phenoxyethoxy)pyrazine (50 mg, 0.20 mmol; from Example 1, Step 1) and N,N′-dimethylethylenediamine (0.2 mL, 1.9 mmol) was heated in a MicroWell 10 microwave reactor for 6 min at 100W. The reaction mixture was partitioned between water and EtOAc and applied to a hydromatrix column. The column was eluted with EtOAc and the elute was concentrated. The product was purified by Amberchrom CG-161m LC using CH3CN/H2O (gradient: CH3CN 0% to 100%). Yield 2 mg (4%). MS m/z 303 (M+H)+.

Workup

  1. customThe reaction mixture was partitioned between water and EtOAc
  2. washThe column was eluted with EtOAc
  3. concentrationthe elute was concentrated
  4. customThe product was purified by Amberchrom CG-161m LC

Sources & evidence

ORD record
ord-729a5675a6924126b4e783634c52af09
Source dataset
uspto-grants-2009_05
Patent number
US07534794B2

Reaction notes

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