1,2-Dichloroethane → HCID 86761041, compound

HRID 1992797Notes

Reaction equation

HRID 1992797 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:14]=[C:13]([C:15]([OH:17])=O)[NH:12][N:11]=2)[CH:5]=[C:6]([F:9])[C:7]=1[F:8].[F:18][C:19]([F:29])([F:28])[O:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1.CCN(C(C)C)C(C)C.C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.C(OCC)(=O)C>[F:18][C:19]([F:28])([F:29])[O:20][C:21]1[CH:22]=[CH:23][C:24]([NH:25][C:15]([C:13]2[NH:12][N:11]=[C:10]([C:4]3[CH:5]=[C:6]([F:9])[C:7]([F:8])=[C:2]([F:1])[CH:3]=3)[CH:14]=2)=[O:17])=[CH:26][CH:27]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 6008484-(Trifluoromethoxy)anilineHCID 68428139HCID 68428139, compound

Product 1

HCID 86761041HCID 86761041, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the intermediate from step D (0.1 g, 0.41 mmol) in DMF (2 mL) was added 4-trifluoromethoxy aniline (83 μL, 0.61 mmol), DIEA (215 μL, 1.23 mmol), HOAt (0.08 g, 0.61 mmol) and EDC (0.118 g, 0.61 mmol). The reaction was heated at 50° C. for 3 hours. The reaction was diluted with ethyl acetate, washed with 1N HCl , saturated NaHCO3, and saturated NaCl solutions. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography using 30% ethyl acetate hexanes. 1H NMR (DMSO, 500 MHz): 10.34 (bs, 1H), 7.93 (d, J=5.9 Hz, 2H), 7.8 (bm, 2H), 7.44 (bs, 1H), 7.37 (bd, J=8.0 Hz, 2H). LC-MS=3.76 min; (M+H)=402.

Workup

  1. washwashed with 1N HCl , saturated NaHCO3, and saturated NaCl solutions
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography
  6. customLC-MS=3.76 min

Sources & evidence

ORD record
ord-01ded6e49f1047839ba094d839d771ac
Source dataset
uspto-grants-2010_01
Patent number
US07649009B2

Reaction notes

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