Potassium Carbonate → 6-((((2S,3R)-3-Methyl-1-(5-methyl-2-(1-methyl-1H-pyrazol-4-yl)benzoyl)piperidin-2-yl)methyl)amino)nicotinonitrile

HRID 60966Notes

Reaction equation

HRID 60966 reaction equation
[NH2:1][CH2:2][C@@H:3]1[C@H:8]([CH3:9])[CH2:7][CH2:6][CH2:5][N:4]1[C:10]([C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:13]=1[C:19]1[CH:20]=[N:21][N:22]([CH3:24])[CH:23]=1)=[O:11].Cl[C:26]1[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[CH:28][N:27]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:9][C@@H:8]1[CH2:7][CH2:6][CH2:5][N:4]([C:10](=[O:11])[C:12]2[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:13]=2[C:19]2[CH:20]=[N:21][N:22]([CH3:24])[CH:23]=2)[C@@H:3]1[CH2:2][NH:1][C:26]1[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[CH:28][N:27]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 117728145((2S,3R)-2-(Aminomethyl)-3-methylpiperidin-1-yl)(5-methyl-2-(1-methyl-1H-pyrazol-4-yl)phenyl)methanone

Product 1

HCID 1177280936-((((2S,3R)-3-Methyl-1-(5-methyl-2-(1-methyl-1H-pyrazol-4-yl)benzoyl)piperidin-2-yl)methyl)amino)nicotinonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ((2S,3R)-2-(aminomethyl)-3-methylpiperidin-1-yl)(5-methyl-2-(1-methyl-1H-pyrazol-4-yl)phenyl)methanone (80 mg, 245 μmol), 6-chloronicotinonitrile (50 mg, 368 μmol) and anhydrous K2CO3 (102 mg, 735 μmol) in DMF (2 mL) was heated at 100° C. overnight. The mixture was cooled to rt and the solvent was removed in vacuo. The crude was dissolved in EtOAc and washed with satd. NaHCO3, brine and then dried (MgSO4). The solvent was removed and the crude was purified by reverse-phase preparative HPLC to afford the title compound. MS (ESI) 429 (M+H).

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 satd
  5. dry with materialNaHCO3, brine and then dried (MgSO4)
  6. customThe solvent was removed
  7. customthe crude was purified by reverse-phase preparative HPLC

Sources & evidence

ORD record
ord-682a0d65ed3c43969c791b4eeea63b86
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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