Piperazine → HCID 66740677, compound

HRID 1027872Notes

Reaction equation

HRID 1027872 reaction equation
[NH2:1][C:2]1[N:17]=[C:16](OS(C2C=CC(C)=CC=2)(=O)=O)[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:4]=2[N:3]=1.[NH:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.C(N(CC)CC)C>C(#N)C>[N:29]1([C:16]2[C:5]3[CH2:6][CH2:7][CH2:8][CH2:9][C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=4[C:4]=3[N:3]=[C:2]([NH2:1])[N:17]=2)[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 8471TriethylamineHCID 87741738HCID 87741738, compound

Product 1

HCID 66740677HCID 66740677, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of Example 20C (80 mg 0.20 mmol), piperazine (26 mg, 0.30 mmol) and triethylamine (0.1 mL, 0.72 mmol) in anhydrous acetonitrile (3 mL) was heated at 160° C. in a microwave reactor for 20 minutes. The mixture was concentrated under reduced pressure and chromatographed on silica gel eluting with NH4OH:MeOH:CH2Cl2 (0.6:6:94) to provide the title compound. 1H NMR (CD3OD) δ 1.45 (m, 2H), 1.86 (m, 1H), 2.00-2.15 (m, 2H), 2.34 (m, 1H), 2.73 (dd, J=14.58, 8.48 Hz, 1H), 2.80-3.02 (m, 5H), 3.37 (m, 4H), 7.22 (m, 1H), 7.24-7.31 (m, 2H), 7.33-7.41 (m, 1H). MS (M+H)+ m/z 310.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customchromatographed on silica gel eluting with NH4OH:MeOH:CH2Cl2 (0.6:6:94)

Sources & evidence

ORD record
ord-93b1a9e329a4482d8d84d97b336f7ed7
Source dataset
uspto-grants-2014_05
Patent number
US08735411B2

Reaction notes

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