Diisopropylethylamine → (S)-N-(5-(4-chlorophenyl)-6-(1,1,1-trifluoropropan-2-yloxy)pyridin-3-yl)pyridazine-3-carboxamide
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([OH:9])=O)[N:2]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)C(C)C)C.[Cl:41][C:42]1[CH:47]=[CH:46][C:45]([C:48]2[CH:49]=[C:50]([NH2:61])[CH:51]=[N:52][C:53]=2[O:54][C@@H:55]([CH3:60])[C:56]([F:59])([F:58])[F:57])=[CH:44][CH:43]=1>CN(C=O)C>[Cl:41][C:42]1[CH:43]=[CH:44][C:45]([C:48]2[CH:49]=[C:50]([NH:61][C:7]([C:3]3[N:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[O:9])[CH:51]=[N:52][C:53]=2[O:54][C@@H:55]([CH3:60])[C:56]([F:57])([F:58])[F:59])=[CH:46][CH:47]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Pyridazine-3-carboxylic acid (CAN 2164-61-6; 43.1 mg, 347 μmol) was suspended in DMF (1.0 mL). TBTU (112 mg, 347 μmol), ethyldiisopropylamine (102 mg, 131 μl, 789 μmol,) and 5-(4-chloro-phenyl)-6-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-pyridin-3-ylamine (0.100 g, 316 μmol) were added and the reaction mixture was stirred at room temperature for 1 h. The rection mixture was extracted with ethyl acetate and 1M citric acid solution; the organic phase was dried with MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 10 g, 10% to 50% ethyl acetate in heptane) to give 0.11 g (83%) of the title compound as white solid; MS (EI) 423.1 (M+H)+.
Workup
- extractionThe rection mixture was extracted with ethyl acetate and 1M citric acid solution
- dry with materialthe organic phase was dried with MgSO4
- concentrationconcentrated in vacuo
- customThe crude material was purified by flash chromatography (silica gel, 10 g, 10% to 50% ethyl acetate in heptane)
Sources & evidence
- ORD record
- ord-b31475174256454ca03c72527d637cbb
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08410107B2
Reaction notes
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