1-Methylpiperazine → HCID 16039641, compound

HRID 252073Notes

Reaction equation

HRID 252073 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:24]2[CH:25]=[C:26]([CH2:30]OS(C)(=O)=O)[CH:27]=[N:28][CH:29]=2)[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=1)[CH2:7]2.[CH3:36][N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1>C1COCC1.O>[NH3:8].[CH3:1][C:2]1[CH:3]=[C:4]([C:24]2[CH:29]=[N:28][CH:27]=[C:26]([CH2:30][N:40]3[CH2:41][CH2:42][N:37]([CH3:36])[CH2:38][CH2:39]3)[CH:25]=2)[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH2:12][C:13]1[CH:14]=[CH:15][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:17][CH:18]=1)[CH2:7]2

Participants

6

Reactant 2

HCID 531671-MethylpiperazineHCID 57949692HCID 57949692, compound

Product 2

HCID 222AmmoniaYield 5%HCID 16039641HCID 16039641, compoundYield 132.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Methanesulfonic acid 5-[7-methyl-1-oxo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-1H-isoindol-5-yl]-pyridin-3-ylmethyl ester (36 mg, 0.071 mmol) was dissolved in THF (5 mL). N-Methyl piperazine (24 uL, 0.213 mmol) was added and the mixture stirred at 50° C. for 18 hrs. The mixture was cooled, diluted with water, and extracted with ethyl acetate. The organics were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. Column chromatography (5% 2M NH3 in MeOH/CH2Cl2) provided the title compound (24 mg, 67%) as a yellow oil. 1H NMR (300 MHz, CDCl3): δ 8.73 (s, 1H), 8.56 (s, 1H), 7.86 (s, 1H), 7.42 (d, 2H), 7.37 (d, 2H), 7.19 (d, 2H), 4.82 (s, 2H), 4.32 (s, 2H), 3.60 (s, 2H), 2.85 (s, 3H), 2.52-2.42 (br s, 8H), 2.30 (s, 3H).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe organics were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7da5dab666474a288f44abf49935bf8f
Source dataset
uspto-grants-2011_01
Patent number
US07868008B2

Reaction notes

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