Hydrazine hydrate (1:1) → ((2S,3R)-2-(Aminomethyl)-3-methylpiperidin-1-yl)(5-(4-fluorophenyl)-2-methylthiazol-4-yl)methanone

HRID 60912Notes

Reaction equation

HRID 60912 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([CH3:13])=[N:10][C:9]=2[C:14]([N:16]2[CH2:21][CH2:20][CH2:19][C@@H:18]([CH3:22])[C@H:17]2[CH2:23][N:24]2C(=O)C3C(=CC=CC=3)C2=O)=[O:15])=[CH:4][CH:3]=1.O.NN>CO>[NH2:24][CH2:23][C@@H:17]1[C@H:18]([CH3:22])[CH2:19][CH2:20][CH2:21][N:16]1[C:14]([C:9]1[N:10]=[C:11]([CH3:13])[S:12][C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)=[O:15]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 1177280582-(((2S,3R)-1-(5-(4-fluorophenyl)-2-methylthiazole-4-carbonyl)-3-methylpiperidin-2-yl)methyl)isoindoline-1,3-dione

Product 1

HCID 89739171((2S,3R)-2-(Aminomethyl)-3-methylpiperidin-1-yl)(5-(4-fluorophenyl)-2-methylthiazol-4-yl)methanone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(((2S,3R)-1-(5-(4-fluorophenyl)-2-methylthiazole-4-carbonyl)-3-methylpiperidin-2-yl)methyl)isoindoline-1,3-dione (130 mg, 272 μmol) and hydrazine hydrate (67 μL, 1.36 mmol) in MeOH (3 mL) was heated at reflux for 2 h. The mixture was cooled and the solvent was removed in vacuo. The crude was dissolved in EtOAc and washed with 2 N NaOH (2×) and brine. The organic solution was dried over anhydrous Na2SO4. The solvent was removed to obtain the title compound which was used without further purification. MS (ESI) 348 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. temperatureThe mixture was cooled
  4. customthe solvent was removed in vacuo
  5. dissolutionThe crude was dissolved in EtOAc
  6. washwashed with 2 N NaOH (2×) and brine
  7. dry with materialThe organic solution was dried over anhydrous Na2SO4
  8. customThe solvent was removed

Sources & evidence

ORD record
ord-f9ff297827b94a8a88077c9a8395542e
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

Loading…