Trifluoroacetic acid → HCID 68678774, compound
Reaction equation
FC(F)(F)C(O)=O.Cl.Cl.C([NH:17][C:18]1[CH:46]=[CH:45][C:21]([NH:22][C:23]2[C:32]3[C:27](=[CH:28][C:29]([O:35][CH2:36][CH2:37][CH2:38][N:39]4[CH2:44][CH2:43][O:42][CH2:41][CH2:40]4)=[C:30]([O:33][CH3:34])[CH:31]=3)[N:26]=[CH:25][N:24]=2)=[CH:20][CH:19]=1)(OC(C)(C)C)=O>ClCCl>[NH2:17][C:18]1[CH:19]=[CH:20][C:21]([NH:22][C:23]2[C:32]3[C:27](=[CH:28][C:29]([O:35][CH2:36][CH2:37][CH2:38][N:39]4[CH2:40][CH2:41][O:42][CH2:43][CH2:44]4)=[C:30]([O:33][CH3:34])[CH:31]=3)[N:26]=[CH:25][N:24]=2)=[CH:45][CH:46]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Trifluoroacetic acid (1.00 ml, 13.1 mmol) was added to a suspension of 4-(4-(N-Boc-amino)anilino)-6-methoxy-7-(3-morpholinopropoxy)quinazoline dihydrochloride (100 mg, 0.172 mmol) in dichloromethane (2.0 ml) and the reaction stirred for 1 hour at ambient temperature. The solvents were removed in vacuo, the residue was suspended in water (2.0 ml) and saturated aqueous sodium bicarbonate solution (4.0 ml) was added. The aqueous phase was extracted with dichloromethane (3×10 ml) and the combined organic layers were washed with brine (25 ml) and evaporated in vacuo. Drying of the solid in vacuo yielded 4-(4-aminoanilino)-6-methoxy-7-(3-morpholinopropoxy)quinazoline (53 mg, 75% yield) as a white solid:
Workup
- customThe solvents were removed in vacuo
- additionsaturated aqueous sodium bicarbonate solution (4.0 ml) was added
- extractionThe aqueous phase was extracted with dichloromethane (3×10 ml)
- washthe combined organic layers were washed with brine (25 ml)
- customevaporated in vacuo
- customDrying of the solid in vacuo
Sources & evidence
- ORD record
- ord-05c064a9f43a43f6b7b0c86bcfad5cd5
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07709479B1
Reaction notes
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