1-Methylpiperazine → HCID 136005862, compound

HRID 915939Notes

Reaction equation

HRID 915939 reaction equation
[CH:1]1([C:7]2[C:15]3[C:14](=[O:16])[NH:13][C:12]([C:17]4[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[CH:19][C:18]=4[O:26][CH3:27])=[N:11][C:10]=3[N:9]([CH3:28])[N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:29][N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.Cl.C(N=C=NCCCN(C)C)C.C(=O)([O-])O.[Na+]>ClCCl>[CH:1]1([C:7]2[C:15]3[C:14](=[O:16])[NH:13][C:12]([C:17]4[CH:25]=[CH:24][C:20]([C:21]([N:33]5[CH2:34][CH2:35][N:30]([CH3:29])[CH2:31][CH2:32]5)=[O:22])=[CH:19][C:18]=4[O:26][CH3:27])=[N:11][C:10]=3[N:9]([CH3:28])[N:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 531671-MethylpiperazineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 136005769HCID 136005769, compound

Product 1

HCID 136005862HCID 136005862, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 2 ml dichloromethane suspension of 86 mg (0.23 mmol) of the compound obtained in Example 65, 31 μl (0.28 mmol) of N-methylpiperazine and 53 mg (0.28 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride were added, and the mixture was stirred at room temperature for 18 hours. Then, an aqueous solution of sodium hydrogen carbonate was added to the reaction mixture, and the mixture was extracted with dichloromethane. The organic layer was washed with water and a saturated aqueous solution of sodium chloride. After the washed layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=20/1˜10/1) to obtain 80 mg (75%) of the captioned compound.

Workup

  1. additionwere added
  2. extractionthe mixture was extracted with dichloromethane
  3. washThe organic layer was washed with water
  4. dry with materialAfter the washed layer was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform/methanol=20/1˜10/1)

Sources & evidence

ORD record
ord-b4fa832a764b46cf9985554ed7bb3e3e
Source dataset
uspto-grants-2007_09
Patent number
US07268128B2

Reaction notes

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