Piconol → HCID 11188865, compound

HRID 550067Notes

Reaction equation

HRID 550067 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][OH:8].[H-].[Na+].Cl[C:12]1[N:13]=[CH:14][C:15]([C:18]([NH:20][C:21]2[CH:26]=[C:25]([C:27]([NH:29][CH:30]3[CH2:32][CH2:31]3)=[O:28])[CH:24]=[CH:23][C:22]=2[CH3:33])=[O:19])=[N:16][CH:17]=1>CN1C(=O)CCC1>[CH:30]1([NH:29][C:27]([C:25]2[CH:24]=[CH:23][C:22]([CH3:33])=[C:21]([NH:20][C:18]([C:15]3[CH:14]=[N:13][C:12]([O:8][CH2:7][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)=[CH:17][N:16]=3)=[O:19])[CH:26]=2)=[O:28])[CH2:32][CH2:31]1

Participants

5

Reactant 3

HCID 11474PiconolHCID 24758Sodium hydrideHCID 86612959HCID 86612959, compound

Product 1

HCID 11188865HCID 11188865, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To 2-pyridinylmethanol (300 μL) was added sodium hydride 60% dispersion in oil (20 mg, 1.39 mmol) under inert atmosphere and the mixture stirred at room temperature for 10 minutes. NMP (600 μL) was then added followed by 5-chloro-N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-2-pyrazinecarboxamide (100 mg, 0.303 mmol) and the resulting mixture stirred for 48 hours. The solvent was evaporated under reduced pressure and the residue partitioned between saturated aqueous sodium bicarbonate and DCM. Evaporation of DCM, precipitation with diethyl ether and isohexanes and filtration gave the title compound as a solid (25 mg, 20%); NMR Spectrum: (DMSOd6) 0.58 (m, 2H), 0.69 (m, 2H), 2.31 (s, 3H), 2.86 (m, 1H), 5.59 (s, 2H), 7.36 (m, 2H), 7.55 (m, 1H), 7.62 (d, 1H), 7.86 (m, 1H), 8.08 (m, 1H), 8.37 (m, 1H), 8.58 (m, 2H), 8.89 (s, 1H), 9.76 (s, 1H); Mass Spectrum: M+H+ 404.

Workup

  1. stirringthe resulting mixture stirred for 48 hours
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue partitioned between saturated aqueous sodium bicarbonate and DCM
  4. customEvaporation of DCM, precipitation
  5. filtrationwith diethyl ether and isohexanes and filtration

Sources & evidence

ORD record
ord-cd5021ed069b492a96b2bd037ef38e9b
Source dataset
uspto-grants-2011_05
Patent number
US07943776B2

Reaction notes

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