Triethylsilane → Osi-930

HRID 2112787Notes

Reaction equation

HRID 2112787 reaction equation
[F:1][C:2]([F:20])([F:19])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[S:14][CH:15]=[CH:16][C:17]=2[NH2:18])=[O:12])=[CH:6][CH:5]=1.[N:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]([CH:31]=O)=[CH:23][CH:22]=1.C([SiH](CC)CC)C>FC(F)(F)C(O)=O.ClCCl>[F:20][C:2]([F:19])([F:1])[O:3][C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11]([C:13]2[S:14][CH:15]=[CH:16][C:17]=2[NH:18][CH2:31][C:24]2[C:25]3[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:21]=[CH:22][CH:23]=2)=[O:12])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 780724-QuinolinecarboxaldehydeHCID 219638853-amino-N-(4-(trifluoromethoxy)phenyl)thiophene-2-carboxamide

Product 1

HCID 9868037Osi-930

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of N-(4-trifluoromethoxyphenyl) 3-aminothiophene-2-carboxamide (1 g, 3.3 1 mmol) and quinoline-4-carboxaldehyde (347 mg, 2.21 mmol) in trifluoroacetic acid:dichloromethane (1:1, 30 mL) was heated at reflux for 2 h under nitrogen. The reaction was cooled to RT and triethylsilane (0.71 mL, 4.42 mmol) was added. The resulting solution was then stirred at reflux for 16 h under nitrogen. After cooling to RT, the reaction mixture was evaporated under reduced pressure and the residue was partitioned between ethyl acetate (3×100 mL) and saturated sodium bicarbonate solution (50 mL). The organic layers were dried over Na2SO4, filtered, and concentrated. The residue was purified by silica gel chromatography (20-30% ethyl acetate in hexane) to give EXAMPLE 1 as a light yellow solid, mp: 168-170° C.

Workup

  1. temperatureat reflux for 2 h under nitrogen
  2. temperatureat reflux for 16 h under nitrogen
  3. temperatureAfter cooling to RT
  4. customthe reaction mixture was evaporated under reduced pressure
  5. customthe residue was partitioned between ethyl acetate (3×100 mL) and saturated sodium bicarbonate solution (50 mL)
  6. dry with materialThe organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography (20-30% ethyl acetate in hexane)
  10. customto give EXAMPLE 1 as a light yellow solid, mp: 168-170° C.

Sources & evidence

ORD record
ord-82882b2367e04965bb1c5ecb4f54ea5c
Source dataset
uspto-grants-2009_04
Patent number
US07524859B2

Reaction notes

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