Ethyl Acetate → T6787352

HRID 887175Notes

Reaction equation

HRID 887175 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 (DCI/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-0c880243be334b12bd27a4f21f6b24a2
Source dataset
uspto-grants-2012_08
Patent number
US08247413B2

Reaction notes

Loading…