1,2-Dichloroethane → HCID 178522672, compound

HRID 1992793Notes

Reaction equation

HRID 1992793 reaction equation
CO[C:3]([C:5]1[CH:28]=[CH:27][C:8]([CH2:9][N:10]2[C:14]([C:15]([OH:17])=O)=[CH:13][C:12]([C:18]3[CH:23]=[C:22]([F:24])[C:21]([F:25])=[C:20]([F:26])[CH:19]=3)=[N:11]2)=[CH:7][CH:6]=1)=[O:4].[F:29][C:30]([F:40])([F:39])[O:31][C:32]1[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=1.C1C=[N:45][C:44]2[N:47](O)[N:48]=[N:49]C=2C=1.CC[N:53](C(C)C)C(C)C.C(Cl)CCl>CN(C=O)C.C(OCC)(=O)C>[NH:47]1[C:44]([NH:53][C:3]([C:5]2[CH:28]=[CH:27][C:8]([CH2:9][N:10]3[C:14]([C:15]([NH:36][C:35]4[CH:37]=[CH:38][C:32]([O:31][C:30]([F:39])([F:40])[F:29])=[CH:33][CH:34]=4)=[O:17])=[CH:13][C:12]([C:18]4[CH:19]=[C:20]([F:26])[C:21]([F:25])=[C:22]([F:24])[CH:23]=4)=[N:11]3)=[CH:7][CH:6]=2)=[O:4])=[N:45][N:49]=[N:48]1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 6008484-(Trifluoromethoxy)anilineHCID 68427678HCID 68427678, compound

Product 1

HCID 178522672HCID 178522672, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the intermediate from example 1 step D (0.39 g, 1.0 mmol) in DMF (2 mL) was added 4-trifluromethoxy aniline (83 μL, 0.615 mmol), HOAt (0.2 g, 1.5 mmol), DIEA (0.52 mL, 3.0 mmol) and EDC (0.29 g, 1.5 mmol). The resulting solution was stirred at room temperature for 48 hours. The reaction was diluted with ethyl acetate and washed with 1N HCl, saturated NaHCO3, and saturated NaCl. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified on Biotage Quad 3 system using 30% ethyl acetate-hexanes to give the title compound. 1H NMR (CDCl3, 500 MHz): 8.03 (d, J=8.3 Hz, 2H), 7.72 (s, 1H), 7.64 (d, J=8.9 Hz, 2H), 7.49 (t, J=6.9 Hz, 2H), 7.43 (d, J=8.2 Hz, 2H), 7.29 (d, J=8.7 Hz, 2H), 6.96 (s, 1H), 5.91 (s, 2H), 3.93 (s, 3H). LC-MS: 4.32 min; (M+H)=550.1.

Workup

  1. washwashed with 1N HCl, saturated NaHCO3, and saturated NaCl
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified on Biotage Quad 3 system

Sources & evidence

ORD record
ord-acb99567b68c42a6a88c05847d725a46
Source dataset
uspto-grants-2010_01
Patent number
US07649009B2

Reaction notes

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