1,2-Ethanediamine, N1,N1,N2-trimethyl- → HCID 86687243, compound

HRID 630943Notes

Reaction equation

HRID 630943 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH2:17])[N:8]([C:10]2[CH:15]=[CH:14][N:13]=[C:12](Cl)[N:11]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:18][N:19]([CH3:24])[CH2:20][CH2:21][NH:22][CH3:23]>CC(O)C>[NH2:17][C:7]1[N:8]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([N:22]([CH3:23])[CH2:21][CH2:20][N:19]([CH3:24])[CH3:18])[N:11]=2)[N:9]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]=1

Participants

4

Reactant 2

HCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 86687242HCID 86687242, compound

Product 1

HCID 86687243HCID 86687243, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of Intermediate 140a (250 mg, 0.99 mmol) and N,N,N′-trimethylethylenediamine (0.32 mL, 2.48 mmol) in IPA (2.5 mL) was heated to 120° C. for 10 mins under microwave irradiation. The cooled reaction mixture was concentrated in vacuo and the residue was partitioned between EtOAc and water. The phases were separated and the aqueous layer was extracted with EtOAc (×2). The combined organic phase was washed with brine, dried (Na2SO4) and concentrated in vacuo to give the title compound (0.31 g, quant.) as a golden oil that was used in the next step without purification. LCMS (Method 3): Rt 2.51 min, m/z 318.3 [MH+].

Workup

  1. customThe cooled reaction mixture
  2. concentrationwas concentrated in vacuo
  3. customthe residue was partitioned between EtOAc and water
  4. customThe phases were separated
  5. extractionthe aqueous layer was extracted with EtOAc (×2)
  6. washThe combined organic phase was washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4795c1eaf12749d1ad0c22918c9c7e24
Source dataset
uspto-grants-2016_04
Patent number
US09315503B2

Reaction notes

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