Water → 3-Chloro-1-(3-methylbutyl)-4-[4-(tetrahydropyran-4-ylamino)-phenyl]-1H-pyridin-2-one

HRID 1024389Notes

Reaction equation

HRID 1024389 reaction equation
[CH3:1][CH:2]([CH3:25])[CH2:3][CH2:4][N:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:13][CH:12]=2)=[CH:7][C:6]1=[O:24].[Cl:26]N1C(=O)CCC1=O.O>CN(C=O)C>[Cl:26][C:7]1[C:6](=[O:24])[N:5]([CH2:4][CH2:3][CH:2]([CH3:25])[CH3:1])[CH:10]=[CH:9][C:8]=1[C:11]1[CH:16]=[CH:15][C:14]([NH:17][CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 594977621-(3-Methylbutyl)-4-[4-(tetrahydropyran-4-ylamino)-phenyl]-1H-pyridin-2-one

Product 1

HCID 252213143-Chloro-1-(3-methylbutyl)-4-[4-(tetrahydropyran-4-ylamino)-phenyl]-1H-pyridin-2-oneYield 28%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of intermediate D8 (0.65 g, 1.91 mmol) and N-chlorosuccinimide (0.25 g, 1.91 mmol) in DMF (10 ml) was stirred at 45° C. for 16 hours. After cooling to room temperature water was added and the solution was extracted with EtOAc, The organic layer was separated and washed with brine, dried (Na2SO4) and the solvent evaporated in vacuo. The crude product was purified by column chromatography (silica gel; DCM/EtOAc 8:2 as eluent). The desired fractions were collected and evaporated in vacuo to yield E1 (0.20 g, 28%) as a pale pink solid.

Workup

  1. additionwas added
  2. extractionthe solution was extracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. customthe solvent evaporated in vacuo
  7. customThe crude product was purified by column chromatography (silica gel; DCM/EtOAc 8:2 as eluent)
  8. customThe desired fractions were collected
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-bca537ea3528443fb7326a5a0753bea6
Source dataset
uspto-grants-2014_05
Patent number
US08722894B2

Reaction notes

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