Ethyl Acetate → T6787352

HRID 2056794Notes

Reaction equation

HRID 2056794 reaction equation
[CH2:1]1[CH2:11][CH2:10][N:9]2[C:4](=[N:5][CH2:6][CH2:7][CH2:8]2)[CH2:3][CH2:2]1.[F:12][C:13]1[CH:14]=[C:15]([CH2:19][CH2:20][NH2:21])[CH:16]=[CH:17][CH:18]=1.[C:22](OCC)(=[O:24])C>C(#N)C>[F:12][C:13]1[CH:14]=[C:15]([CH2:19][CH2:20][NH:21][C:22]([NH:5][C:4]2[CH:3]=[CH:2][CH:1]=[C:11]3[C:6]=2[CH:7]=[CH:8][N:9]=[CH:10]3)=[O:24])[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 5339282-(3-Fluorophenyl)ethanamine

Product 1

HCID 9839628T6787352Yield 65%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The product from Example 1A (0.65 g, 2.25 mmol), DBU (0.85 g, 5.6 mmol) and 2-(3-fluorophenyl)ethylamine (0.35 g, 2.5 mmol) in acetonitrile (50 mL) were refluxed for 10 hours. The mixture was cooled, concentrated, diluted with ethyl acetate, washed twice with aqueous ammonium chloride and concentrated to dryness. The solid obtained was suspended in ethyl acetate and filtered to obtain 0.45 g (65%) of the title compound as a tan solid. 1H NMR (300 MHz, d6-DMSO) δ 9.27 (s, 1H), 8.63 (s, 1H), 8.51 (d, 1H), 8.26 (d, 1H), 7.89 (d, 1H), 7.71.(d, 1H), 7.59 (m, 1H), 7.35 (m, 1H), 7.18-7.0 (m, 3H), 6.60 (t, 1H), 3.42 (m, 2H), 2.72 (m, 2H); MS (DCl/NH3) m/z 310 (M+H)+; Anal. Calcd. For C18H16N3FO. 0.1H2O: C, 69.48; H, 5.25; N, 13.51. Found: C, 69.31; H, 5.25; N, 13.46.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. additiondiluted with ethyl acetate
  4. washwashed twice with aqueous ammonium chloride
  5. concentrationconcentrated to dryness
  6. customThe solid obtained
  7. filtrationfiltered

Sources & evidence

ORD record
ord-054f04850f2145d4bc3fa20d0da7eaa5
Source dataset
uspto-grants-2008_02
Patent number
US07335678B2

Reaction notes

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