HCID 10055409, compound → HCID 10347968, compound

HRID 1986644Notes

Reaction equation

HRID 1986644 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:44][S:45]([CH3:48])(=[O:47])=[O:46])[C:8]([O:42][CH3:43])=[C:9]([NH:11][C:12]([C:14]2[S:18][C:17]3[C:19]([NH:23][C:24](=[O:41])[C:25]4[CH:30]=[CH:29][C:28]([NH:31]CC5C=CC(OC)=CC=5)=[N:27][CH:26]=4)=[CH:20][CH:21]=[CH:22][C:16]=3[CH:15]=2)=[O:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>FC(F)(F)C(O)=O>[NH2:31][C:28]1[CH:29]=[CH:30][C:25]([C:24]([NH:23][C:19]2[C:17]3[S:18][C:14]([C:12](=[O:13])[NH:11][C:9]4[CH:10]=[C:5]([C:1]([CH3:3])([CH3:4])[CH3:2])[CH:6]=[C:7]([NH:44][S:45]([CH3:48])(=[O:47])=[O:46])[C:8]=4[O:42][CH3:43])=[CH:15][C:16]=3[CH:22]=[CH:21][CH:20]=2)=[O:41])=[CH:26][N:27]=1

Participants

3

Reactant 1

HCID 10055409HCID 10055409, compound

Product 1

HCID 10347968HCID 10347968, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
75 °C

Procedure

To N-[2-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenylcarbamoyl)-benzo[b]thiophen-7-yl]-6-(4-methoxy-benzylamino)-nicotinamide (Example 1) (20 mg) in a sealed tube was added 90 μL of trifluoroacetic acid. The clear solution was purged with Ar and then heated to 75° C. in a sealed tube 12 h. The reaction was cooled to room temperature and diluted with toluene to remove excess trifluoroacetic acid in vacuo. The resulting trifluoroacetic acid salt of the desired product was dissolved in EtOAc and washed with saturated NaHCO3 solution and brine. The organics were dried over MgSO4, filtered and concentrated to give a foam which was further purified by flash chromatography on silica gel (7%-10% MeOH/CH2Cl2) to provide the title compound as a white solid (14 mg, 85% yield), m.p. 234-235° C.

Workup

  1. customThe clear solution was purged with Ar
  2. temperatureThe reaction was cooled to room temperature
  3. additiondiluted with toluene
  4. customto remove excess trifluoroacetic acid in vacuo
  5. dissolutionThe resulting trifluoroacetic acid salt of the desired product was dissolved in EtOAc
  6. washwashed with saturated NaHCO3 solution and brine
  7. dry with materialThe organics were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give a foam which
  11. customwas further purified by flash chromatography on silica gel (7%-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-d6a2c8dd5f944fc7bdc04f9e0fae8f14
Source dataset
uspto-grants-2009_06
Patent number
US07550461B2

Reaction notes

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