3-Aminopyridine → 2-{[(4-Fluorophenyl)methyl]oxy}-5-{1-[2-(methyloxy)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.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[F:41][C:42]1[CH:47]=[CH:46][C:45]([CH2:48][O:49][C:50]2[CH:59]=[CH:58][C:57]([C:60]3[CH:61]=[N:62][N:63]([CH2:65][CH2:66][O:67][CH3:68])[CH:64]=3)=[CH:56][C:51]=2[C:52](OC)=[O:53])=[CH:44][CH:43]=1>CN(C)C=O>[F:41][C:42]1[CH:47]=[CH:46][C:45]([CH2:48][O:49][C:50]2[CH:59]=[CH:58][C:57]([C:60]3[CH:61]=[N:62][N:63]([CH2:65][CH2:66][O:67][CH3:68])[CH:64]=3)=[CH:56][C:51]=2[C:52]([NH:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[O:53])=[CH:44][CH:43]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
3-Pyridinamine (49.0 mg, 0.52 mmol), HATU (148 mg, 0.39 mmol) and diisopropylethylamine (0.11 ml, 0.65 mmol) were added to a solution of methyl 2-{[(4-fluorophenyl)methyl]oxy}-5-{1-[2-(methyloxy)ethyl]-1H-pyrazol-4-yl}benzoate (may be prepared as described in Description 116; 100 mg, 0.26 mmol) in N,N-dimethylformamide (5 ml) and the mixture was stirred at room temperature overnight. The DMF was evaporated under reduced pressure on a buchi. Water (5 ml) and ethyl acetate (10 ml) were added to the residue. The organics were separated and the aqueous layer was further extracted with ethyl acetate (3×10 ml). The organics were combined and evaporated. The residue was purified using MDAP to yield the title compound. 36 mg.
Workup
- customThe DMF was evaporated under reduced pressure on a buchi
- additionWater (5 ml) and ethyl acetate (10 ml) were added to the residue
- customThe organics were separated
- extractionthe aqueous layer was further extracted with ethyl acetate (3×10 ml)
- customevaporated
- customThe residue was purified
Sources & evidence
- ORD record
- ord-4d2d298b391e40e09229de859a69cfd4
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08778939B2
Reaction notes
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