1-Methylpiperazine → HCID 57625425, compound

HRID 331207Notes

Reaction equation

HRID 331207 reaction equation
Cl[CH2:2][C:3]1[N:8]=[CH:7][C:6]([S:9]([NH:12][C:13]2[C:22]([NH:23][C:24]3[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[C:26]([O:32][CH3:33])[CH:25]=3)=[N:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(N(C(C)C)C(C)C)C.[CH3:43][N:44]1[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]1>C(#N)C.C(Cl)Cl>[CH3:33][O:32][C:26]1[CH:25]=[C:24]([NH:23][C:22]2[C:13]([NH:12][S:9]([C:6]3[CH:7]=[N:8][C:3]([CH2:2][N:47]4[CH2:48][CH2:49][N:44]([CH3:43])[CH2:45][CH2:46]4)=[CH:4][CH:5]=3)(=[O:10])=[O:11])=[N:14][C:15]3[C:20]([N:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=1

Participants

6

Reactant 3

HCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 57625404HCID 57625404, compound

Product 1

HCID 57625425HCID 57625425, compoundYield 9.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

6-(chloromethyl)-N-{3-[(3,5-dimethoxyphenyl)amino]quinoxalin-2-yl}pyridine-3-sulfonamide (100 mg; 0.12 mmol; 1 eq.) and N-ethyl-N-isopropylpropan-2-amine (0.03 ml; 0.25 mmol; 2 eq.) are dissolved in ACN (25 ml) at room temperature then 1-methylpiperazine (0.06 ml; 0.62 mmol; 5 eq.) is added. The reaction mixture is stirred at room temperature for 2 hours. The reaction is quenched by addition of water and neutralized by addition of aqueous Na2CO3. The mixture is concentrated under reduced pressure. The residue obtained is taken up in DCM. The product is extracted with DCM, the organic phase is washed with citric acid 10% then dried over MgSO4. After evaporation of the solvent, the crude residue obtained is purified by flash chromatography to afford 6 mg (9%) of the title compound as a white powder. 1H NMR (DMSO-d6) δ 9.17 (d, J=3 Hz, 1H), 8.30 (m, 1H), 8.24 (dd, J=9 and 3 Hz, 1H), 7.72 (dd. J=9 and 3 Hz, 1H), 7.63 (d, J=9 Hz, 1H), 7.44-7.38 (m, 3H). 7.15 (d, J=3 Hz, 2H), 6.27 (m, 1H), 3.85 (s, 6H), 3.75 (s, 2H), 2.57 (m, 8H), 2.52 (s, 3H). HPLC (max plot) 90%, Rt 3.34 min. LC/MS: MS: (ES+) 550.5, (ES−): 548.5.

Workup

  1. customThe reaction is quenched by addition of water
  2. additionneutralized by addition of aqueous Na2CO3
  3. concentrationThe mixture is concentrated under reduced pressure
  4. customThe residue obtained
  5. extractionThe product is extracted with DCM
  6. washthe organic phase is washed with citric acid 10%
  7. dry with materialthen dried over MgSO4
  8. customAfter evaporation of the solvent
  9. customthe crude residue obtained
  10. customis purified by flash chromatography

Sources & evidence

ORD record
ord-4c046b34c0354502b0deef4ee054f144
Source dataset
uspto-grants-2014_11
Patent number
US08877757B2

Reaction notes

Loading…