Water → HCID 69732326, compound

HRID 2182133Notes

Reaction equation

HRID 2182133 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][NH:6][C:7]1[CH:12]=[N:11][CH:10]=[C:9](Cl)[N:8]=1.[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].N12CCCN=C1CCCCC2.O>C(O)C>[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][N:27]([C:9]2[CH:10]=[N:11][CH:12]=[C:7]([NH:6][CH2:5][C:4]3[CH:14]=[CH:15][CH:16]=[C:2]([Cl:1])[CH:3]=3)[N:8]=2)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 143452tert-Butyl piperazine-1-carboxylateHCID 22482074HCID 22482074, compound

Product 1

HCID 69732326HCID 69732326, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (3-chloro-benzyl)-(6-chloro-pyrazin-2-yl)-amine (I-2a) (71.0 mg, 0.28 mmol), piperazine-1-carboxylic acid tert-butyl ester (260.2 mg, 1.40 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (208.9 μL, 1.40 mmol) in 1.0 mL of ethanol was refluxed for 18 h under nitrogen. The reaction was then cooled to ambient temperature and poured into 20 mL of water. This was extracted 2×30 mL of ethyl acetate and the combined organic extracts were washed with 3×15 mL water followed by 15 mL of brine. The organic layer was then dried over sodium sulfate, filtered and concentrated in vacuo to a yellow residue that was chromatographed (prep. TLC, 1:1 hexane:ethyl acetate) to give the title compound (I-2b) as a white solid, 13.5 mg.

Workup

  1. temperaturewas refluxed for 18 h under nitrogen
  2. extractionThis was extracted 2×30 mL of ethyl acetate
  3. washthe combined organic extracts were washed with 3×15 mL water
  4. dry with materialThe organic layer was then dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to a yellow residue that
  7. customwas chromatographed (prep. TLC, 1:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-49a5cee1df4c448395b88e88c61dbb02
Source dataset
uspto-grants-2005_05
Patent number
US06894050B2

Reaction notes

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