Potassium Hydroxide → HCID 67974717, compound

HRID 706576Notes

Reaction equation

HRID 706576 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.[CH3:9][C@@H:10]1[N:15]([CH3:16])[CH2:14][CH2:13][N:12]([CH2:17][CH2:18][OH:19])[CH2:11]1.[OH-].[K+]>CS(C)=O.O>[CH3:9][C@@H:10]1[N:15]([CH3:16])[CH2:14][CH2:13][N:12]([CH2:17][CH2:18][O:19][C:2]2[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=2)[CH2:11]1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 5818662-Amino-4-chloropyridineHCID 67975003(S)-2-(3,4-dimethylpiperazin-1-yl)ethanol

Product 1

HCID 67974717HCID 67974717, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

4-Chloropyridin-2-amine (0.500 g, 3.89 mmol), (S)-2-(3,4-dimethylpiperazin-1-yl)ethanol (1.23 g, 7.78 mmol), and crushed potassium hydroxide (0.546 g, 9.72 mmol) were combined in 8 mL of DMSO in a pressure tube and heated to 95° C. for 16 hours. The mixture was then diluted with water (100 mL), extracted 2 times with EtOAc, extracts washed with brine, dried and concentrated under reduced pressure. Column chromatography (5% MeOH/DCM) afforded 0.484 g (50%) of the title compound.

Workup

  1. extractionextracted 2 times with EtOAc
  2. washextracts washed with brine
  3. customdried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-27442d51757749fda1f33e25ad693a3f
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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