Potassium tert-butoxide → 4-(4-Cyano-2-methoxyphenyl)-6-methyl-5-(4-methyl-1,3-thiazol-2-yl)-2-(trifluoromethyl)-1,4-di-hydropyridine-3-carbonitrile
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[CH:11]=[C:12]([C:16]1[S:17][CH:18]=[C:19]([CH3:21])[N:20]=1)[C:13](=O)[CH3:14])[C:6]#[N:7].[NH2:22][C:23]([C:27]([F:30])([F:29])[F:28])=[CH:24][C:25]#[N:26].CC(C)([O-])C.[K+]>C(O)(C)C>[C:6]([C:5]1[CH:8]=[CH:9][C:10]([CH:11]2[C:12]([C:16]3[S:17][CH:18]=[C:19]([CH3:21])[N:20]=3)=[C:13]([CH3:14])[NH:22][C:23]([C:27]([F:30])([F:29])[F:28])=[C:24]2[C:25]#[N:26])=[C:3]([O:2][CH3:1])[CH:4]=1)#[N:7]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
100 mg (0.335 mmol) of the compound from example 6A, 46 mg (0.335 mmol) of 3-amino-4,4,4-tri-fluorobut-2-enenitrile [preparation in analogy to U.S. Pat. No. 3,635,977 and K. Krespan, J. Org. Chem. 34, 42-45 (1969)] and 5.6 mg (0.05 mmol) of potassium tert-butoxide are dissolved in 4 ml of isopropanol and stirred at the reflux temperature overnight. After cooling to room temperature, the volatile components are removed in a rotary evaporator, and the crude product is purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80→95:5). 119 mg (82% of theory) of the title compound are obtained.
Workup
- customthe volatile components are removed in a rotary evaporator
- customthe crude product is purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80→95:5)
Sources & evidence
- ORD record
- ord-540c4b52c5f54c788317ed5455e23334
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08404723B2
Reaction notes
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