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Potassium Carbonate → 3-cyclopentyl-2-[4-(3-fluoro-pyridin-2-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid methyl ester

HRID 2381377
Notes
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Reaction equation

HRID 2381377 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH:4]([N:11]1[C:16](=[O:17])[CH:15]=[C:14](I)[CH:13]=[N:12]1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[F:20][C:21]1[C:22]([OH:27])=[N:23][CH:24]=[CH:25][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][O:2][C:3](=[O:19])[CH:4]([N:11]1[C:16](=[O:17])[CH:15]=[C:14]([O:27][C:22]2[C:21]([F:20])=[CH:26][CH:25]=[CH:24][N:23]=2)[CH:13]=[N:12]1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 668748863-cyclopentyl-2-(4-iodo-6-oxo-6H-pyridazin-1-yl)-propionic acid methyl esterHCID 178517712HCID 178517712, compound

Product 1

HCID 668754893-cyclopentyl-2-[4-(3-fluoro-pyridin-2-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid methyl esterYield 53%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
120 °C

Procedure

A solution of 3-cyclopentyl-2-(4-iodo-6-oxo-6H-pyridazin-1-yl)-propionic acid methyl ester (0.38 g, 1 mmol) in N,N-dimethylformamide (10 mL) was treated with 3-fluoro-pyridin-2-ol (0.15 g, 1 mmol) and potassium carbonate (0.16 g, 1.2 mmol). The reaction was heated at 120° C. for 4 h and then concentrated in vacuo. The residue was partitioned between water and methylene chloride. The aqueous layer was back extracted with methylene chloride. The combined organics were washed with a saturated aqueous sodium chloride solution, and then concentrated in vacuo. Chromatography (1/1 ethyl acetate/petroleum ether) afforded 3-cyclopentyl-2-[4-(3-fluoro-pyridin-2-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid methyl ester (0.19 g, 53%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between water and methylene chloride
  3. extractionThe aqueous layer was back extracted with methylene chloride
  4. washThe combined organics were washed with a saturated aqueous sodium chloride solution
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c1e758e022f840d9bf17e085e8f31fb9
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08258134B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes