4-Methylmorpholine → 4-[3-(3-Trifluoromethoxy-benzoylamino)-benzylamino]-quinazoline-8-carboxylic acid amide
Reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:12]=[CH:11][C:7](C(O)=O)=[CH:6][CH:5]=1.CCN=C=NCCC[N:23]([CH3:25])C.Cl.C1C=CC2N([OH:36])N=NC=2C=1.CN1CCOCC1.N[C:45]1[CH:65]=[CH:64][CH:63]=[CH:62][C:46]=1[CH2:47][NH:48][C:49]1[C:58]2[C:53](=[C:54]([C:59]([NH2:61])=[O:60])[CH:55]=[CH:56][CH:57]=2)[N:52]=[CH:51][N:50]=1>CN(C=O)C>[F:14][C:2]([F:1])([F:13])[O:3][C:4]1[CH:5]=[C:6]([CH:7]=[CH:11][CH:12]=1)[C:25]([NH:23][C:65]1[CH:45]=[C:46]([CH:62]=[CH:63][CH:64]=1)[CH2:47][NH:48][C:49]1[C:58]2[C:53](=[C:54]([C:59]([NH2:61])=[O:60])[CH:55]=[CH:56][CH:57]=2)[N:52]=[CH:51][N:50]=1)=[O:36]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
22.3 mg (0.1 mmol) 4-trifluoromethoxy-benzoic acid were dissolved in 1 ml DMF. 41.8 mg (0.2 mmol) EDCl, 15.0 mg (0.1 mmol) HOBt and 48.5 μl (0.4 mmol) 4-methylmorpholine were added and the mixture was stirred for 15 min. Subsequently, 50 mg (0.1 mmol) 4-(2-Amino-benzylamino)-quinazoline-8-carboxylic acid amide were added and the mixture was stirred overnight at room temperature. The reaction mixture was purified using preparative HPLC and converted into the hydrochloride salt by treatment with excess HCl in methanol. 18.3 mg, off-white solid.
Workup
- stirringthe mixture was stirred overnight at room temperature
- customThe reaction mixture was purified
Sources & evidence
- ORD record
- ord-ee305b561fe74b78ab23c068981f9706
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08637532B2
Reaction notes
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