Triethylamine → HCID 66616382, compound

HRID 1917272Notes

Reaction equation

HRID 1917272 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[C:5]([C:10](=O)[C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1)=[CH:6]N(C)C)[CH3:2].Cl.[F:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]([NH2:31])=[NH:30])=[CH:24][CH:23]=1.CCN(CC)CC>CCO.O>[CH2:1]([O:3][C:4]([C:5]1[C:10]([C:11]2[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=2)=[N:30][C:29]([CH2:28][C:25]2[CH:24]=[CH:23][C:22]([F:21])=[CH:27][CH:26]=2)=[N:31][CH:6]=1)=[O:19])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 17221602(4-Fluorophenyl)ethanimidamide--hydrogen chloride (1/1)HCID 66616462HCID 66616462, compound

Product 1

HCID 66616382HCID 66616382, compoundYield 74.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To solution of 3-dimethylamino-2-(4-methyl-benzoyl)-acrylic acid ethyl ester (Tetrahedron, 2002, 58, 8581-8589; 0.567 g, 2.15 mmol) in EtOH (10 mL) was added 2-(4-fluoro-phenyl)-acetamidine hydrochloride (0.405 g, 2.15 mmol) and Et3N (0.90 mL, 6.5 mmol). The mixture was heated at reflux for 18 h, and then was diluted with water and extracted with EtOAc (2×). The combined organic layers were dried and concentrated. The resulting residue was purified via SiO2 chromatography (5-20% EtOAc/hexanes) to give 0.560 g (74%) of the title compound. MS (ESI): exact mass calcd. for C21H19FN2O2, 350.14; m/z found, 351.4 [M+H]+. H NMR (CDCl3): 8.97 (s, 1H), 7.51 (d, J=8.2, 2H), 7.38-7.35 (m, 2H), 7.27-7.26 (m, 2H), 7.01-6.97 (m, 2H), 4.32 (s, 2H), 4.23 (q, J=7.1, 2H), 2.42 (s, 3H), 1.16 (t, J=7.1, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 18 h
  3. extractionextracted with EtOAc (2×)
  4. customThe combined organic layers were dried
  5. concentrationconcentrated
  6. customThe resulting residue was purified via SiO2 chromatography (5-20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ba81dc511ff74ff5aec0d6983ad80690
Source dataset
uspto-grants-2013_12
Patent number
US08618288B2

Reaction notes

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