1,2-Dichloroethane → 2-{[(4-Fluorophenyl)methyl]oxy}-5-{1-[2-(4-morpholinyl)ethyl]-1H-pyrazol-4-yl}-N-3-pyridinylbenzamide
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[CH:2]=1.ON1C2N=CC=CC=2N=N1.C(Cl)CCl.C(N(C(C)C)CC)(C)C.[F:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][O:39][C:40]2[CH:48]=[CH:47][C:46]([C:49]3[CH:50]=[N:51][N:52]([CH2:54][CH2:55][N:56]4[CH2:61][CH2:60][O:59][CH2:58][CH2:57]4)[CH:53]=3)=[CH:45][C:41]=2[C:42](O)=[O:43])=[CH:34][CH:33]=1>CN(C)C=O>[F:31][C:32]1[CH:33]=[CH:34][C:35]([CH2:38][O:39][C:40]2[CH:48]=[CH:47][C:46]([C:49]3[CH:50]=[N:51][N:52]([CH2:54][CH2:55][N:56]4[CH2:61][CH2:60][O:59][CH2:58][CH2:57]4)[CH:53]=3)=[CH:45][C:41]=2[C:42]([NH:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[O:43])=[CH:36][CH:37]=1Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
3-Pyridinamine (26.5 mg, 0.28 mmol), 1-hydroxy-7-azabenzotriazole (30.7 mg, 0.23 mmol), EDC (43.3 mg, 0.23 mmol) and diisopropylethylamine (0.07 ml, 0.38 mmol) were added to a solution of 2-{[(4-fluorophenyl)methyl]oxy}-5-{1-[2-(4-morpholinyl)ethyl]-1H-pyrazol-4-yl}benzoic acid (may be prepared as described in Description 114; 80 mg, 0.19 mmol) in N,N-dimethylformamide (2 ml), and the reaction was stirred at room temperature overnight. The DMF was removed on a buchi. The residue was taken up into ethyl acetate (50 ml), washed with water (1×25 ml). The ethyl acetate layer was evaporated on a buchi under reduced pressure and the residue was purified using the MDAP to yield the title compound. 45 mg.
Workup
- customThe DMF was removed on a buchi
- washwashed with water (1×25 ml)
- customThe ethyl acetate layer was evaporated on a buchi under reduced pressure
- customthe residue was purified
Sources & evidence
- ORD record
- ord-f8fc5d9eec144c94a0bd2fa3cfd811f1
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08778939B2
Reaction notes
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