Water → HCID 67127147, compound

HRID 1035878Notes

Reaction equation

HRID 1035878 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 three 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 three 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-ef612dd2a03240fea7c3495ad433d554
Source dataset
uspto-grants-2013_10
Patent number
US08546399B2

Reaction notes

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