Sodium hydride → HCID 46830921, compound

HRID 1848345Notes

Reaction equation

HRID 1848345 reaction equation
[OH:1][CH2:2][C:3]1([C:6]2[N:24]=[C:9]3[C:10]([O:22][CH3:23])=[CH:11][CH:12]=[C:13]([C:14]4[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=4)[C:17]#[N:18])[N:8]3[N:7]=2)[CH2:5][CH2:4]1.[H-].[Na+].[N:27]1([C:32](Cl)=[O:33])[CH2:31][CH2:30][CH2:29][CH2:28]1.C([O-])(O)=O.[Na+]>CN(C=O)C.O>[C:17]([C:16]1[CH:15]=[C:14]([C:13]2[N:8]3[N:7]=[C:6]([C:3]4([CH2:2][O:1][C:32]([N:27]5[CH2:31][CH2:30][CH2:29][CH2:28]5)=[O:33])[CH2:5][CH2:4]4)[N:24]=[C:9]3[C:10]([O:22][CH3:23])=[CH:11][CH:12]=2)[CH:21]=[CH:20][CH:19]=1)#[N:18]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 709371-Pyrrolidinecarbonyl chlorideHCID 516892Sodium BicarbonateHCID 46830920HCID 46830920, compound2×

Product 1

HCID 46830921HCID 46830921, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Under an argon atmosphere 3-[2-(1-Hydroxymethyl-cyclopropyl)-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-benzonitrile (compound 150) (0.03 g, 0.08 mmol) was dissolved in DMF (0.5 mL). NaH (0.02 g, 0.48 mmol) was added and the suspension was heated at 65° C. for 1 h after which 1-pyrrolidine carbonylchloride (0.088 mL, 0.8 mmol) was added. Stirring was performed at 65° C. for 1 h. The reaction mixture was cooled and aq. NaHCO3 and H2O was added. The aqueous phase was extracted with EtOAc (×2). The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica using DCM:MeOH 99:1 as eluent to afford the title compound as a solid.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was cooled
  3. extractionThe aqueous phase was extracted with EtOAc (×2)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography on silica

Sources & evidence

ORD record
ord-b2d2baa632684bac88e7e650bc8f59c0
Source dataset
uspto-grants-2015_02
Patent number
US08952162B2

Reaction notes

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