Sodium Hydroxide → HCID 9840864, compound

HRID 1828318Notes

Reaction equation

HRID 1828318 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12](S(C3C=CC(C)=CC=3)(=O)=O)[N:11]=[C:10]([CH:23]3[CH2:28][CH2:27][N:26](C(=O)C)[CH2:25][CH2:24]3)[C:9]=2[C:32]2[CH:37]=[CH:36][N:35]=[CH:34][N:33]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:32]3[CH:37]=[CH:36][N:35]=[CH:34][N:33]=3)=[C:10]([CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[NH:11][N:12]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22066046HCID 22066046, compound

Product 1

HCID 9840864HCID 9840864, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

This reaction was conducted in a 250 ml round bottom flask. To 4-{3-(1-acetylpiperidin-4-yl)-5-(4-chlorophenyl)-1-[(4-methylphenyl)sulfonyl]-1H-pyrazole-4-yl}pyrimidine (9) (6.86 g) was added 6 M HCl (40 ml). The mixture was stirred and heated to reflux. The reaction was monitored by HPLC, and determined to be complete after 2.5 hr. The mixture was then cooled in an ice/water bath, and 6 M NaOH was slowly added until the pH was between 13–14. The resulting product was isolated via vacuum filtration to yield 3.25 g of 4-[3-(4-chlorophenyl)-5-piperidine-4-yl-1H-pyrazol-4-yl]pyrimidine (79.8% yield) as a white solid.

Workup

  1. customThis reaction was conducted in a 250 ml round bottom flask
  2. temperatureheated to reflux
  3. temperatureThe mixture was then cooled in an ice/water bath
  4. customThe resulting product was isolated via vacuum filtration

Sources & evidence

ORD record
ord-7aa71b6bed594c30ba2f66032dc49f71
Source dataset
uspto-grants-2006_06
Patent number
US07057049B2

Reaction notes

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