Trifluoroacetic acid → HCID 68678774, compound

HRID 2233247Notes

Reaction equation

HRID 2233247 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=O.C([NH:15][C:16]1[CH:40]=[CH:39][C:19]([NH:20][C:21]2[C:30]3[C:25](=[CH:26][C:27]([O:33][CH2:34][C:35](F)(F)F)=[C:28]([O:31][CH3:32])[CH:29]=3)[N:24]=[CH:23][N:22]=2)=[CH:18][CH:17]=1)(OC(C)(C)C)=O>ClCCl>[NH2:15][C:16]1[CH:40]=[CH:39][C:19]([NH:20][C:21]2[C:30]3[C:25](=[CH:26][C:27]([O:33][CH2:34][CH2:35][CH2:21][N:20]4[CH2:2][CH2:3][O:5][CH2:18][CH2:19]4)=[C:28]([O:31][CH3:32])[CH:29]=3)[N:24]=[CH:23][N:22]=2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68677885HCID 68677885, compound

Product 1

HCID 68678774HCID 68678774, compoundYield 234.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (20.0 ml, 260 mmol) was added to a suspension of 4-(4-(N-Boc-amino)anilino)-6-methoxy-7-(2,2,2-trifluoroethoxy)quinazoline (7.50 g, 11.7 mmol) in dichloromethane (80 ml) and the reaction stirred for 45 minutes at ambient temperature. The solvents were removed in vacuo, the residue was suspended in water (50 ml) and saturated aqueous sodium bicarbonate solution was added. The aqueous phase was extracted with ethyl acetate (3×100 ml) and the combined organic layers were washed with brine (100 ml) and evaporated in vacuo. Drying of the solid in vacuo yielded 4-(4-aminoanilino)-6-methoxy-7-(3-morpholinopropoxy)quinazoline (5.62 g, 100% yield) as a yellow solid:

Workup

  1. customThe solvents were removed in vacuo
  2. additionsaturated aqueous sodium bicarbonate solution was added
  3. extractionThe aqueous phase was extracted with ethyl acetate (3×100 ml)
  4. washthe combined organic layers were washed with brine (100 ml)
  5. customevaporated in vacuo
  6. customDrying of the solid in vacuo

Sources & evidence

ORD record
ord-ae2453226fa64033951582406cbe65eb
Source dataset
uspto-grants-2010_05
Patent number
US07709479B1

Reaction notes

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