Pyridine → HCID 11486376, compound

HRID 1822935Notes

Reaction equation

HRID 1822935 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[N:7]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)[N:6]=[CH:5][CH:4]=1.C(Cl)(C(Cl)=O)=O.N1C=CC=CC=1.[F:31][C:32]([F:41])([F:40])[C:33]1[CH:39]=[CH:38][C:36]([NH2:37])=[CH:35][CH:34]=1>CN(C=O)C.C(Cl)Cl.CN(C1C=CN=CC=1)C.Cl>[F:31][C:32]([F:40])([F:41])[C:33]1[CH:34]=[CH:35][C:36]([NH:37][C:12](=[O:14])[C:11]2[CH:10]=[CH:9][C:8]([N:7]3[C:3]([C:2]([F:1])([F:18])[F:17])=[CH:4][CH:5]=[N:6]3)=[CH:16][CH:15]=2)=[CH:38][CH:39]=1

Participants

9

Reactant 4

HCID 1049PyridineHCID 99644-(Trifluoromethyl)anilineHCID 65578Oxalyl chlorideHCID 22170448HCID 22170448, compound

Product 1

HCID 11486376HCID 11486376, compound

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 142844-(Dimethylamino)pyridineCatalystHCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

The product from Example 37A (69.8 mg, 0.272 mmol) and DMF (1 drop) in CH2Cl2 (2 mL) was treated with (COCl)2 (29 mL, 0.33 mmol). After stirring for 5 hours, the mixture was concentrated and the residue dissolved in CH2Cl2 (2 mL). The mixture was treated with DMAP (35.8 mg, 0.29 mmol), pyridine (22 mL, 0.27 mmol), and 4-trifluoromethylaniline (41 mL, 0.33 mmol). The mixture was heated at 60° C. for 15 hours, allowed to cool to room temperature, diluted with 1N HCl (4 mL), extracted with CH2Cl2 (2×4 mL), dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (15% ethyl acetate in hexanes) to provide the title compound as a solid. 1H NMR (300 MHz, CDCl3) δ 8.02 (d, 2H), 7.93 (br s, 1H), 7.80 (d, 2H), 7.77 (m, 1H), 7.68 (d, 2H), 7.66(d, 2H), 6.88 (m, 1H); MS (m/z) 400, 417.

Workup

  1. concentrationthe mixture was concentrated
  2. dissolutionthe residue dissolved in CH2Cl2 (2 mL)
  3. temperatureto cool to room temperature
  4. extractionextracted with CH2Cl2 (2×4 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under reduced pressure
  8. customThe residue was purified by flash chromatography (15% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-987ec1bf47184453b53f71d7bcdc516a
Source dataset
uspto-grants-2006_05
Patent number
US07037927B2

Reaction notes

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