1-Methylpiperazine → HCID 86757740, compound

HRID 1251078Notes

Reaction equation

HRID 1251078 reaction equation
[F:1][C:2]1([F:34])[CH2:3][CH2:4][N:5]([C:17]([C:19]2[CH:20]=[N:21][N:22](C3C=CC=CC=3)[C:23]=2[C:24]([F:27])([F:26])[F:25])=[O:18])[C:6]2[CH:16]=[CH:15][CH:14]=[CH:13][C:7]=2/[C:8]/1=[CH:9]/[C:10]([OH:12])=O.ON1[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=2N=N1.[ClH:45].C(N=C=NCCCN(C)C)C.[CH3:57][N:58]1[CH2:63][CH2:62][NH:61][CH2:60][CH2:59]1.C(=O)(O)[O-].[Na+]>O1CCCC1>[ClH:45].[F:34][C:2]1([F:1])[CH2:3][CH2:4][N:5]([C:17]([C:19]2[CH:20]=[N:21][N:22]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:23]=2[C:24]([F:26])([F:27])[F:25])=[O:18])[C:6]2[CH:16]=[CH:15][CH:14]=[CH:13][C:7]=2/[C:8]/1=[CH:9]/[C:10]([N:61]1[CH2:62][CH2:63][N:58]([CH3:57])[CH2:59][CH2:60]1)=[O:12]

Participants

7

Reactant 5

HCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 70160797HCID 70160797, compound

Product 1

HCID 86757740HCID 86757740, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 200 mg of (Z)-[4,4-difluoro-1-(1-phenyl-5-trifluoromethyl-1H-pyrazole-4-carbonyl)-2,3,4,5-tetrahydro-1H-1-benzoazepin-5-ylidene]acetic acid in 20 ml of tetrahydrofuran were added 90 mg of 1-hydroxybenzotriazole, 130 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide monohydrochloride and 60 mg of 1-methylpiperazine, and the mixture was stirred at room temperature for 18 hours. A saturated aqueous solution of sodium bicarbonate was added to the reaction solution, followed by extracting with ethyl acetate. The organic layer was washed with a saturated aqueous solution of NaCl and dried over magnesium sulfate, followed by evaporating off the solvent. The residue was purified by silica gel column chromatography (eluting with chloroform-methanol). The resulting residue (190 mg) was dissolved in 5 ml of chloroform, and 0.5 ml of a 4N HCl/ethyl acetate solution was added thereto, followed by stirring at room temperature. The solvent was evaporated off, and the residue was crystallized from ethanol-diethyl ether to give 190 mg of (Z)-4,4-difluoro-5-[2-(4-methylpiperazin-1-yl)-2-oxoethylidene]-1-(1-phenyl-5-trifluoromethyl-1H-pyrazole-4-carbonyl)-2,3,4,5-tetrahydro-1H-1-benzoazepine monohydrochloride as a colorless powder.

Workup

  1. extractionby extracting with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of NaCl
  3. dry with materialdried over magnesium sulfate
  4. customby evaporating off the solvent
  5. customThe residue was purified by silica gel column chromatography (eluting with chloroform-methanol)
  6. dissolutionThe resulting residue (190 mg) was dissolved in 5 ml of chloroform
  7. addition0.5 ml of a 4N HCl/ethyl acetate solution was added
  8. stirringby stirring at room temperature
  9. customThe solvent was evaporated off
  10. customthe residue was crystallized from ethanol-diethyl ether

Sources & evidence

ORD record
ord-cc6749716adf442aaa3311c8b42c06a1
Source dataset
uspto-grants-2002_01
Patent number
US06340678B1

Reaction notes

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