Piperazine → HCID 68760129, compound

HRID 79585Notes

Reaction equation

HRID 79585 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.F[C:8]1[C:13]([O:14][CH:15]([CH3:17])[CH3:16])=[CH:12][N:11]=[C:10]2[NH:18][CH:19]=[CH:20][C:9]=12>CN1C(=O)CCC1>[CH:15]([O:14][C:13]1[C:8]([N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)=[C:9]2[CH:20]=[CH:19][NH:18][C:10]2=[N:11][CH:12]=1)([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 68760650HCID 68760650, compound

Product 1

HCID 68760129HCID 68760129, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
200 °C

Procedure

Piperazine (222 mg, 2.6 mmol) was added to 4-fluoro-5-isopropoxy-1H-pyrrolo[2,3-b]pyridine (50 mg, 0.26 mmol) in NMP (1 mL), and the reaction was heated to 200° C. for 1 hour under microwave irradiation. The reaction was concentrated to dryness under high vacuum and then purified by chromatography (SP4, 12+M, water/ACN 100/0→40/60, 20CV) to yield 5-isopropoxy-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine (33 mg, 49% yield) as an oil.

Workup

  1. concentrationThe reaction was concentrated to dryness under high vacuum
  2. custompurified by chromatography (SP4, 12+M, water/ACN 100/0→40/60, 20CV)

Sources & evidence

ORD record
ord-03383e9b3c794013be15867cea59c6e5
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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