Water → HCID 67127147, compound

HRID 574775Notes

Reaction equation

HRID 574775 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[C:8]([O:10][C:11]3[CH:20]=[C:19](F)[CH:18]=[CH:17][C:12]=3[C:13]([O:15][CH3:16])=[O:14])[CH:9]=[C:4]2[CH:3]=[CH:2]1.[NH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.O>CS(C)=O>[NH:1]1[C:5]2=[N:6][CH:7]=[C:8]([O:10][C:11]3[CH:20]=[C:19]([N:22]4[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]4)[CH:18]=[CH:17][C:12]=3[C:13]([O:15][CH3:16])=[O:14])[CH:9]=[C:4]2[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 4837PiperazineHCID 66713127Methyl 4-Fluoro-2-{1H-pyrrolo[2,3-b]pyridin-5-yloxy}benzoate

Product 1

HCID 67127147HCID 67127147, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of EXAMPLE 3H (20.5 g) and piperazine (37.0 g) in dimethylsulfoxide (200 mL) was heated to 110° C. for 24 hours, and the mixture was allowed to cool to room temperature. The mixture was poured into water (1 L), extracted thee times with dichloromethane, and the combined extracts were washed with 2× water, and brine and filtered and concentrated to give the pure product.

Workup

  1. extractionextracted thee times with dichloromethane
  2. washthe combined extracts were washed with 2× water, and brine
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give the pure product

Sources & evidence

ORD record
ord-50ac33aa643843d3b1dfa919017fac74
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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