2-Butenoic acid, 3-(acetylamino)-, methyl ester, (2Z)- → HCID 90031429, compound

HRID 56133Notes

Reaction equation

HRID 56133 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[CH:12][CH:11]=[N:10]1)[NH2:5].C[Al](C)C.[NH:18](/[C:22](/[CH3:28])=[CH:23]\[C:24](OC)=[O:25])[C:19]([CH3:21])=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([N:5]2[C:24](=[O:25])[CH:23]=[C:22]([CH3:28])[N:18]=[C:19]2[CH3:21])[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[CH:12][CH:11]=[N:10]1

Participants

5

Reactant 3

HCID 57053602-Butenoic acid, 3-(acetylamino)-, methyl ester, (2Z)-HCID 10725981[3-fluoro-4-(1H-pyrazol-1-yl)phenyl]amineHCID 16682925Trimethylaluminum

Product 1

HCID 90031429HCID 90031429, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-fluoro-4-(1H-pyrazol-1-yl)aniline (0.65 g, 3.68 mmol) in CH2Cl2 (30 mL) was added trimethylaluminum (18.4 mL, 36.8 mmol, 2 M in heptane) slowly. The reaction mixture was stirred at rt for 0.5 h, followed by the addition of a solution of methyl 3-acetaminocrotonate (634 mg, 4.04 mmol) in CH2Cl2 (10 mL). The reaction was stirred at rt for 3 days, then quenched with saturated NH4Cl aqueous solution and extracted with CH2Cl2 (100 mL×3). The combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:2) to give the title compound as a white solid (400 mg, 38%). The compound was characterized by the following spectroscopic data:

Workup

  1. stirringThe reaction was stirred at rt for 3 days
  2. customquenched with saturated NH4Cl aqueous solution
  3. extractionextracted with CH2Cl2 (100 mL×3)
  4. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:2)

Sources & evidence

ORD record
ord-1130a2caf7234c7985bf0a17021fd670
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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