2-Butenoic acid, 3-(acetylamino)-, methyl ester, (2Z)- → HCID 72950004, compound

HRID 56186Notes

Reaction equation

HRID 56186 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][NH:9][C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][C:11]=2[F:17])[CH:5]=[CH:4][N:3]=[CH:2]1.C[Al](C)C.[NH:22](/[C:26](/[CH3:32])=[CH:27]\[C:28](OC)=[O:29])[C:23]([CH3:25])=O>C(Cl)Cl>[N:1]1([CH2:6][CH2:7][CH2:8][NH:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[C:28](=[O:29])[CH:27]=[C:26]([CH3:32])[N:22]=[C:23]3[CH3:25])=[CH:12][C:11]=2[F:17])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 57053602-Butenoic acid, 3-(acetylamino)-, methyl ester, (2Z)-HCID 16682925TrimethylaluminumHCID 28993591HCID 28993591, compound

Product 1

HCID 72950004HCID 72950004, compoundYield 15.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N1-(3-(1H-imidazol-1-yl)propyl)-2-fluorobenzene-1,4-diamine (1.00 g, 4.27 mmol) in CH2Cl2 (30 mL) was added trimethylaluminium (16.4 mL, 32.8 mmol, 2 M in toluene) slowly. The mixture was stirred at rt for 0.5 h, followed by the addition of a solution of methyl 3-acetaminocrotonate (1.00 g, 6.36 mmol) in CH2Cl2 (8 mL). The reaction mixture was stirred at rt for 24 h, then quenched with saturated NH4Cl aqueous solution and extracted with CH2Cl2 (50 mL×3). The combined organic phases were washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/MeOH (V/V)=20:1) to give the title compound as pale yellow oil (0.22 g, 15%). The compound was characterized by the following spectroscopic data:

Workup

  1. stirringThe reaction mixture was stirred at rt for 24 h
  2. customquenched with saturated NH4Cl aqueous solution
  3. extractionextracted with CH2Cl2 (50 mL×3)
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by a silica gel column chromatography (DCM/MeOH (V/V)=20:1)

Sources & evidence

ORD record
ord-21d054e95d2042d1942ef69a4b05468e
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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