Ethyl 3-(4-Fluorophenyl)-3-Oxopropanoate → HCID 136393900, compound

HRID 872124Notes

Reaction equation

HRID 872124 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)=[C:8]([NH2:17])[NH:7][N:6]=1)[CH3:2].[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:25](=O)[CH2:26][C:27](OCC)=[O:28])=[CH:21][CH:20]=1>N1C=CC=CC=1>[CH2:1]([O:3][CH2:4][C:5]1[C:9]([C:10]2[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=2)=[C:8]2[NH:17][C:27](=[O:28])[CH:26]=[C:25]([C:22]3[CH:23]=[CH:24][C:19]([F:18])=[CH:20][CH:21]=3)[N:7]2[N:6]=1)[CH3:2]

Participants

4

Reactant 2

HCID 2758844Ethyl 3-(4-Fluorophenyl)-3-OxopropanoateHCID 178467667HCID 178467667, compound

Product 1

HCID 136393900HCID 136393900, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-(Ethoxymethyl)-4-(4-methylphenyl)-1H-pyrazol-5-amine (133 mg) and ethyl 3-(4-fluorophenyl)-3-oxopropanoate (0.2 mL) are stirred at 84° C. for 14 hours in a pyridine (10 mL) solvent. After cooling to room temperature, the reaction solvent is removed by distillation under reduced pressure. The remainder is extracted with ethyl acetate and water. The extracted organic layer is washed with brine and dehydrated with anhydrous MgSO4. The dehydrated organic layer is distilled under reduced pressure and purified by column chromatography to yield 132 mg of the target compound. 1H NMR (CDCl3, 300 MHz): δ 10.08 (s, 1H), 7.98 (m, 2H), 7.28 (m, 4H), 7.13 (m, 2H), 4.43 (s, 2H), 4.04 (br, 1H), 3.50 (m, 2H), 2.35 (s, 3H), 1.06 (t, 3H).

Workup

  1. customthe reaction solvent is removed by distillation under reduced pressure
  2. extractionThe remainder is extracted with ethyl acetate and water
  3. washThe extracted organic layer is washed with brine
  4. distillationThe dehydrated organic layer is distilled under reduced pressure
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-70d1c7dd86c84cd29c40ef57602b7d88
Source dataset
uspto-grants-2015_03
Patent number
US08975264B2

Reaction notes

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