Hydrazine hydrate (1:1) → (1-(Aminomethyl)hexahydrocyclopenta[c]pyrrol-2(1H)-yl)(5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone

HRID 60997Notes

Reaction equation

HRID 60997 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N:30]2[N:34]=[CH:33][CH:32]=[N:31]2)=[C:6]([CH:29]=1)[C:7]([N:9]1[CH2:13][CH:12]2[CH2:14][CH2:15][CH2:16][CH:11]2[CH:10]1[CH2:17][N:18]1C(=O)C2C(=CC=CC=2)C1=O)=[O:8].O.NN>CO>[NH2:18][CH2:17][CH:10]1[CH:11]2[CH2:16][CH2:15][CH2:14][CH:12]2[CH2:13][N:9]1[C:7]([C:6]1[CH:29]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=1[N:30]1[N:34]=[CH:33][CH:32]=[N:31]1)=[O:8]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 1177276222-((2-(5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoyl)octahydrocyclopenta[c]pyrrol-1-yl)methyl)isoindoline-1,3-dione

Product 1

HCID 117727999(1-(Aminomethyl)hexahydrocyclopenta[c]pyrrol-2(1H)-yl)(5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-((2-(5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoyl)octahydrocyclopenta[c]pyrrol-1-yl)methyl)isoindoline-1,3-dione (1 equiv.) and hydrazine monohydrate (4 equiv.) in MeOH (0.5M) was stirred at 70° C. for 3 h and then concentrated in vacuo to a yellow oil. The reaction mixture was diluted with EtOAc and washed with water, brine, dried (MgSO4), and concentrated. The crude residue was purified by chromatography on silica gel (20% MeOH in EtOAc) to firstly remove the impurities and then (2:8:1 MeOH/EtOAc/TEA) to elute the title compound which was concentrated to yield a yellow oil. MS (ESI) 326 (M+H).

Workup

  1. concentrationconcentrated in vacuo to a yellow oil
  2. additionThe reaction mixture was diluted with EtOAc
  3. washwashed with water, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude residue was purified by chromatography on silica gel (20% MeOH in EtOAc)
  7. customto firstly remove the impurities
  8. wash(2:8:1 MeOH/EtOAc/TEA) to elute the title compound which
  9. concentrationwas concentrated
  10. customto yield a yellow oil

Sources & evidence

ORD record
ord-819b90d4b87144a8937054d597a90a90
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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