Piconol → HCID 11188865, compound

HRID 403040Notes

Reaction equation

HRID 403040 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 hrs. 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 hrs
  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-ee46170771b545fcb86fe0084766be8f
Source dataset
uspto-grants-2014_06
Patent number
US08742124B2

Reaction notes

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