Trifluoroacetic anhydride → HCID 59275416, compound

HRID 1877527Notes

Reaction equation

HRID 1877527 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.CCN(C(C)C)C(C)C.[F:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[O:31][C:32]3[CH:41]=[C:40]([NH:42][S:43]([CH3:46])(=[O:45])=[O:44])[C:39]([O:47][CH:48]([CH3:50])[CH3:49])=[CH:38][C:33]=3[C:34]=2[C:35]([NH2:37])=O)=[CH:26][CH:25]=1>C(Cl)Cl.C1COCC1.CCOC(C)=O>[C:35]([C:34]1[C:33]2[CH:38]=[C:39]([O:47][CH:48]([CH3:50])[CH3:49])[C:40]([NH:42][S:43]([CH3:46])(=[O:45])=[O:44])=[CH:41][C:32]=2[O:31][C:30]=1[C:27]1[CH:26]=[CH:25][C:24]([F:23])=[CH:29][CH:28]=1)#[N:37]

Participants

7

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 81531DiisopropylethylamineHCID 59275711HCID 59275711, compound

Product 1

HCID 59275416HCID 59275416, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Trifluoroacetic anhydride (375 μL, 2.66 mmol) was added to a stirring solution of DIEA (928 μL, 5.31 mmol), 2-(4-fluorophenyl)-5-isopropoxy-6 (methylsulfonamido) benzofuran-3-carboxamide (300 mg, 0.738 mmol) in CH2Cl2 (4 mL) and THF (4 mL) at 0° C. for 1 hour. The mixture was diluted with EtOAc and washed with sat NaHCO3, and sat NaCl. The organic phase was dried over Na2SO4, filtered and concentrated. The crude residue was purified by on silica gel (Biotage, gradient EtOAc/hexanes, fraction collection at λ=254 nm) to give the title compound (143 mg, 50%). 1H NMR (300 MHz, DMSO-D6) δ ppm 1.28-1.41 (m, 6H) 3.01 (s, 3H) 4.77-4.95 (m, 1H) 7.35 (s, 1H) 7.44-7.57 (m, 2H) 7.68 (s, 1H) 8.04-8.20 (m, 2H) 9.01 (s, 1H). LC-MS retention time: 1.65 min; m/z (MH−): 387. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Waters XBridge 5 u C18 4.6×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 5 ml/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 2 min, a hold time of 1 min, and an analysis time of 3 min where solvent A was 5% acetonitrile/95% H2O/10 mM ammonium acetate and solvent B was 5% H2O/95% acetonitrile/10 mM ammonium acetate. MS data was determined using a Micromass Platform for LC in electrospray mode.

Workup

  1. washwashed
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified by on silica gel (Biotage, gradient EtOAc/hexanes, fraction collection at λ=254 nm)

Sources & evidence

ORD record
ord-ea40edd95c0b4110a646f5cba794f0da
Source dataset
uspto-grants-2012_11
Patent number
US08309558B2

Reaction notes

Loading…