Hydrazine hydrate (1:1) → ((2S,3R)-2-(Aminomethyl)-3-methylpiperidin-1-yl)(5-methyl-2-(1-methyl-1H-pyrazol-4-yl)phenyl)methanone

HRID 60894

Reaction equation

HRID 60894 reaction equation
[CH3:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8](=[O:22])[C:9]2[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:10]=2[C:16]2[CH:17]=[N:18][N:19]([CH3:21])[CH:20]=2)[C@@H:3]1[CH2:23][N:24]1C(=O)C2C(=CC=CC=2)C1=O.O.NN>CO>[NH2:24][CH2:23][C@@H:3]1[C@H:2]([CH3:1])[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:10]=1[C:16]1[CH:17]=[N:18][N:19]([CH3:21])[CH:20]=1)=[O:22]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 1177277262-(((2S,3R)-3-Methyl-1-(5-methyl-2-(1-methyl-1H-pyrazol-4-yl)benzoyl)piperidin-2-yl)methyl)isoindoline-1,3-dione

Product 1

HCID 117728145((2S,3R)-2-(Aminomethyl)-3-methylpiperidin-1-yl)(5-methyl-2-(1-methyl-1H-pyrazol-4-yl)phenyl)methanone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-(((2S,3R)-3-methyl-1-(5-methyl-2-(1-methyl-1H-pyrazol-4-yl)benzoyl)piperidin-2-yl)methyl)isoindoline-1,3-dione (0.67 g, 1.5 mmol) and hydrazine hydrate (0.46 g, 9.27 mmol) in MeOH (10 mL) was heated at 60° C. for 2 h. The mixture was cooled to rt and the solvent was removed in vacuo. The crude was dissolved in EtOAc and washed with 2 N NaOH (2×), brine, and then dried (Na2SO4). The solvent was removed in vacuo to obtain the title compound which was used without further purification. ESI-MS (m/z): 327 [M+1]+.

Workup

  1. temperatureThe mixture was cooled to rt
  2. customthe solvent was removed in vacuo
  3. dissolutionThe crude was dissolved in EtOAc
  4. washwashed with 2 N NaOH (2×), brine
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-4e3bd81d2a5b4d49bed37df63cd49eb6
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Linked notes

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