HCID 66677892, compound → HCID 66670296, compound

HRID 1514643Notes

Reaction equation

HRID 1514643 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][CH2:14][C:15]1[N:19]([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[C:18]([CH3:29])=[C:17]([C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])[CH:16]=1>C(O)C.O1CCCC1.O.NN>[NH2:3][CH2:12][CH2:13][CH2:14][C:15]1[N:19]([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[C:18]([CH3:29])=[C:17]([C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])[CH:16]=1

Participants

5

Reactant 1

HCID 66677892HCID 66677892, compound

Product 1

HCID 66670296HCID 66670296, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 24654Hydrazine hydrate (1:1)Solvent3×

Procedure

A 1.364 g portion of benzyl 5-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]-1-[2-(4-fluorophenyl)ethyl]-2-methyl-1H-pyrrole-3-carboxylate was dissolved in a mixed solvent of 10 ml ethanol and 10 ml tetrahydrofuran, and 0.139 ml of hydrazine monohydrate was added, followed by stirring at room temperature for 24 hours. Then, 0.252 ml of hydrazine monohydrate was added, followed by stirring at 50° C. for 5 hours. Further, 0.252 ml of hydrazine monohydrate was added, followed by stirring at 50° C. for 20 hours. The reaction liquid was cooled to room temperature and then filtered through celite. The filtrate was concentrated under a reduced pressure, chloroform was added to the residue, and the resulting precipitate was removed by celite-filtration. The filtrate was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (Chromatorex (registered trademark), ethyl acetate) to obtain 850 mg of benzyl 5-(3-aminopropyl)-1-[2-(4-fluorophenyl)ethyl]-2-methyl-1H-pyrrole-3-carboxylate as a colorless oil.

Workup

  1. additionwas added
  2. stirringby stirring at 50° C. for 5 hours
  3. stirringby stirring at 50° C. for 20 hours
  4. customThe reaction liquid
  5. temperaturewas cooled to room temperature
  6. filtrationfiltered through celite
  7. concentrationThe filtrate was concentrated under a reduced pressure, chloroform
  8. additionwas added to the residue
  9. customthe resulting precipitate was removed by celite-filtration
  10. concentrationThe filtrate was concentrated under a reduced pressure
  11. customthe residue was purified by silica gel column chromatography (Chromatorex (registered trademark), ethyl acetate)

Sources & evidence

ORD record
ord-24984b09e01c4aa08410cce39cda6ee0
Source dataset
uspto-grants-2012_07
Patent number
US08222274B2

Reaction notes

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