Acetyl chloride → HCID 68310467, compound

HRID 1021280Notes

Reaction equation

HRID 1021280 reaction equation
[F:1][C:2]1[C:7]([C:8]2[CH:9]=[N:10][C:11]([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)=[N:12][CH:13]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:20][OH:21].[C:22](Cl)(=[O:24])[CH3:23]>ClCCl>[F:1][C:2]1[C:3]([CH2:20][OH:21])=[CH:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH:9]=[N:10][C:11]([CH:14]2[CH2:15][CH2:16][N:17]([C:22](=[O:24])[CH3:23])[CH2:18][CH2:19]2)=[N:12][CH:13]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 86686221HCID 86686221, compound

Product 1

HCID 68310467HCID 68310467, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

{2-Fluoro-3-[2-(piperidin-4-yl)pyrimidin-5-yl]phenyl}methanol (80 mg) was mixed with dichloromethane (1.6 ml), and TEA (85 mg) and acetyl chloride (48 mg) were added thereto at 0° C. The reaction mixture was concentrated under reduced pressure, the residue was mixed with MeOH, and a 1 M aqueous NaOH solution (0.8 ml) was added thereto, followed by stirring for 3 hours. 1 M hydrochloric acid was added to the reaction mixture, and CHCl3/water was added to the reaction liquid. The aqueous layer was extracted with CHCl3, and the prepared organic layer was dried over Na2SO4 and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (CHCl3/MeOH) to obtain 1-(4-{5-[2-fluoro-3-(hydroxymethyl)phenyl]pyrimidin-2-yl}piperidin-1-yl)ethanone (90 mg).

Workup

  1. additionwere added
  2. customat 0° C
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionthe residue was mixed with MeOH
  5. additiona 1 M aqueous NaOH solution (0.8 ml) was added
  6. addition1 M hydrochloric acid was added to the reaction mixture, and CHCl3/water
  7. additionwas added to the reaction liquid
  8. extractionThe aqueous layer was extracted with CHCl3
  9. dry with materialthe prepared organic layer was dried over Na2SO4
  10. concentrationconcentrated under reduced pressure
  11. customThe obtained residue was purified by silica gel column chromatography (CHCl3/MeOH)

Sources & evidence

ORD record
ord-5bc45148bfa844038201de229f5b0777
Source dataset
uspto-grants-2014_05
Patent number
US08716470B2

Reaction notes

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