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Ethyl Acetate → 3-cyclopentyl-2-[6-oxo-4-(4-trifluoromethyl-pyrimidin-2-yloxy)-6H-pyridazin-1-yl]-propionic acid

HRID 2381400
Notes
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Reaction equation

HRID 2381400 reaction equation
C[O:2][C:3](=[O:29])[CH:4]([N:11]1[C:16](=[O:17])[CH:15]=[C:14]([O:18][C:19]2[N:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][N:20]=2)[CH:13]=[N:12]1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Na+].C(OCC)(=O)C>O1CCOCC1>[CH:6]1([CH2:5][CH:4]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([O:18][C:19]3[N:24]=[C:23]([C:25]([F:26])([F:27])[F:28])[CH:22]=[CH:21][N:20]=3)[CH:13]=[N:12]2)[C:3]([OH:29])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 668752343-cyclopentyl-2-[6-oxo-4-(4-trifluoromethyl-pyrimidin-2-yloxy)-6H-pyridazin-1-yl]-propionic acid methyl ester

Product 1

HCID 579191163-cyclopentyl-2-[6-oxo-4-(4-trifluoromethyl-pyrimidin-2-yloxy)-6H-pyridazin-1-yl]-propionic acid

Reagents, catalysts & solvents 1

HCID 31275
1,4-Dioxane
Solvent

Conditions

Temperature
25 °C

Procedure

A solution of 3-cyclopentyl-2-[6-oxo-4-(4-trifluoromethyl-pyrimidin-2-yloxy)-6H-pyridazin-1-yl]-propionic acid methyl ester (0.2 g, 0.48 mmol) in dioxane (2 mL) was treated with a 6N aqueous sodium hydroxide solution (2 mL). The reaction was stirred at 25° C. for 2 d. At this point, ethyl acetate (20 mL) was added and then the aqueous phase was back extracted with ethyl acetate. The combined organics were dried over sodium sulfate, filtered, and concentrated in vacuo. Preparative HPLC afforded 3-cyclopentyl-2-[6-oxo-4-(4-trifluoromethyl-pyrimidin-2-yloxy)-6H-pyridazin-1-yl]-propionic acid as a light oil (20 mg, 10%); 1H NMR (300 MHz, DMSO-d6): δ 9.13 (d, 1H, J=4.8 Hz), 8.24 (d, 1H, J=2.4 Hz), 7.96 (d, 1H, J=4.8 Hz), 7.04 (d, 1H, J=2.4 Hz), 5.38 (dd, 1H, J1=4.5 Hz, J2=10.5 Hz), 2.25˜2.15 (m, 1H), 2.06˜1.97 (m, 1H), 1.71˜1.44 (m, 7H), 1.17˜1.04 (m, 3H). LC-MS: 399.1 [M+1]+, tR=3.04 min.

Workup

  1. extractionthe aqueous phase was back extracted with ethyl acetate
  2. dry with materialThe combined organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-52e28379cbab45f1ac01062c95496535
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