Potassium tert-butoxide → 4-(4-Cyano-2-methoxyphenyl)-6-(methoxymethyl)-5-(4-methyl-1,3-thiazol-2-yl)-2-(trifluoromethyl)-1,4-dihydropyridine-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:18]1[S:19][CH:20]=[C:21]([CH3:23])[N:22]=1)[C:13](=O)[CH2:14][O:15][CH3:16])[C:6]#[N:7].[NH2:24][C:25]([C:29]([F:32])([F:31])[F:30])=[CH:26][C:27]#[N:28].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:18]3[S:19][CH:20]=[C:21]([CH3:23])[N:22]=3)=[C:13]([CH2:14][O:15][CH3:16])[NH:24][C:25]([C:29]([F:32])([F:31])[F:30])=[C:26]2[C:27]#[N:28])=[C:3]([O:2][CH3:1])[CH:4]=1)#[N:7]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
100 mg (0.305 mmol) of the compound from example 14A, 41 mg (0.335 mmol) of 3-amino-4,4,4-trifluorobut-2-enenitrile [preparation in analogy to U.S. Pat. No. 3,635,977 and K. Krespan, J. Org. Chem. 34, 42-45 (1969)] and 5.1 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 material is purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80→95:5). 18 mg (13% of theory) of the title compound are obtained.
Workup
- customthe volatile components are removed in a rotary evaporator
- customthe crude material is purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80→95:5)
Sources & evidence
- ORD record
- ord-4de82e5fa91e42dd91c36d227edfe185
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08404723B2
Reaction notes
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