2-Butenoic acid, 3-(acetylamino)-, methyl ester, (2Z)- → HCID 72950000, compound

HRID 56171Notes

Reaction equation

HRID 56171 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.C[Al](C)C.[NH:24](/[C:28](/[CH3:34])=[CH:29]\[C:30](OC)=[O:31])[C:25]([CH3:27])=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([N:8]2[C:30](=[O:31])[CH:29]=[C:28]([CH3:34])[N:24]=[C:25]2[CH3:27])[CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 57053602-Butenoic acid, 3-(acetylamino)-, methyl ester, (2Z)-HCID 16682925TrimethylaluminumHCID 900228942-fluoro-N1-(4-morpholinobutyl)benzene-1,4-diamine

Product 1

HCID 72950000HCID 72950000, compoundYield 17.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-fluoro-N1-(4-morpholinobutyl)benzene-1,4-diamine (1.07 g, 4.00 mmol) in CH2Cl2 (30 mL) was added trimethylaluminum (14 mL, 28 mmol, 2 M in toluene) slowly at rt. The reaction mixture was stirred at rt for 0.5 h, followed by the addition of a solution of methyl 3-acetaminocrotonate (1.30 g, 8.27 mmol) in CH2Cl2 (5 mL). The reaction mixture was stirred at rt overnight, then quenched with saturated NH4Cl aqueous solution and extracted with CH2Cl2 (50 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)=2:1) to give the title compound as a yellowish solid (0.26 g, 17%). The compound was characterized by the following spectroscopic data:

Workup

  1. stirringThe reaction mixture was stirred at rt overnight
  2. customquenched with saturated NH4Cl aqueous solution
  3. extractionextracted with CH2Cl2 (50 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)=2:1)

Sources & evidence

ORD record
ord-9b58da3bb0c04ee0a4c2c780fd2fe409
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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