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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

HRID 1951546
Notes
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Reaction equation

HRID 1951546 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 534010963-Amino-4,4,4-trifluorobut-2-enenitrileHCID 670179743-Methoxy-4-[2-(4-methyl-1,3-thiazol-2-yl)-3-oxobut-1-en-1-yl]benzonitrile

Product 1

HCID 1357450914-(4-Cyano-2-methoxyphenyl)-6-methyl-5-(4-methyl-1,3-thiazol-2-yl)-2-(trifluoromethyl)-1,4-di-hydropyridine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 3776
Isopropanol
Solvent

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

  1. customthe volatile components are removed in a rotary evaporator
  2. 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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08404723B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes