1,2-Dichloroethane → (E)-2-[2-(1H-indazol-3-yl)vinyl]-N-([1,3,4]thiadiazol-2-yl)benzamide
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14](O)=[O:15])=[N:2]1.[S:21]1[CH:25]=[N:24][N:23]=[C:22]1[NH2:26].C(Cl)CCl.O>C1COCC1.C(OCC)(=O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14]([NH:26][C:22]2[S:21][CH:25]=[N:24][N:23]=2)=[O:15])=[N:2]1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of (E)-2-[2-(1H-indazol-3-yl)vinyl]benzoic acid (0.13 g, 0.49 mmol) obtained in Step 1 of Example 47 in THF (2.6 mL), [1,3,4]thiadiazol-2-ylamine (0.075 g, 0.74 mmol) and EDC (0.18 g, 0.94 mmol) were added, followed by stirring at room temperature for 4.5 hours. The reaction mixture was added with water and ethyl acetate to separate the mixture into organic layer and aqueous layer and the organic layer was concentrated under reduced pressure. The residue was purified by silica gel chromatography (chloroform/methanol=100/0 to 90/10) and the obtained compound was crystallized from ethyl acetate/methanol (1/1, 2.0 mL) to obtain Compound 145 (0.020 g, 12%).
Workup
- customto separate the mixture into organic layer and aqueous layer
- concentrationthe organic layer was concentrated under reduced pressure
- customThe residue was purified by silica gel chromatography (chloroform/methanol=100/0 to 90/10)
- customthe obtained compound was crystallized from ethyl acetate/methanol (1/1, 2.0 mL)
Sources & evidence
- ORD record
- ord-92be3fe0d9a244dc84d6b488b6de9021
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07605272B2
Reaction notes
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