Pyridine → 3-cyano-5-(4'-cyano-benzoylamino)-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamide

HRID 1943122Notes

Reaction equation

HRID 1943122 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:29]#[N:30])[CH:5]=[C:6]([CH:28]=1)[C:7]([NH:9][C:10]1[C:15]([CH3:16])=[CH:14][C:13]([C:17]([F:26])([C:22]([F:25])([F:24])[F:23])[C:18]([F:21])([F:20])[F:19])=[CH:12][C:11]=1[CH3:27])=[O:8].N1C=CC=CC=1.[C:37]([C:39]1[CH:47]=[CH:46][C:42]([C:43](Cl)=[O:44])=[CH:41][CH:40]=1)#[N:38].C(=O)([O-])O.[Na+]>O1CCCC1>[C:29]([C:4]1[CH:5]=[C:6]([CH:28]=[C:2]([NH:1][C:43](=[O:44])[C:42]2[CH:46]=[CH:47][C:39]([C:37]#[N:38])=[CH:40][CH:41]=2)[CH:3]=1)[C:7]([NH:9][C:10]1[C:11]([CH3:27])=[CH:12][C:13]([C:17]([F:26])([C:18]([F:19])([F:20])[F:21])[C:22]([F:23])([F:24])[F:25])=[CH:14][C:15]=1[CH3:16])=[O:8])#[N:30]

Participants

6

Reactant 4

HCID 1049PyridineHCID 801724-Cyanobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 592269545-amino-3-cyano-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamide

Product 1

HCID 866397603-cyano-5-(4'-cyano-benzoylamino)-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamideYield 71.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-amino-3-cyano-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamide (0.199 mg, 0.46 mmol) (Example I9) in tetrahydrofuran (3 ml) were added successively pyridine (0.117 ml, 1.45 mmol) and 4-cyano-benzoyl chloride (80 mg, 0.48 mmol). The reaction mixture was stirred for 2 hours at ambient temperature. Aqueous sodium hydrogen carbonate (saturated) was added and the phases were separated. The aqueous phase was extracted twice with ethyl acetate. The combined organic extracts were dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 2:1) to give Compound No. B1 of Table B (0.186 g, 71.9% yield). 1H-NMR (400 MHz, CHCl3): 8.45 (s, 1H), 8.36 (s, 1H), 8.27 (s, 1H), 8.00 (m, 3H), 7.84 (m, 2H), 7.63 (s, 1H), 7.37 (s, 2H), 2.34 (s, 6H) ppm.

Workup

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted twice with ethyl acetate
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 2:1)
  6. customto give Compound No

Sources & evidence

ORD record
ord-dfb3e581cdbb4238886872c4cfaea386
Source dataset
uspto-grants-2013_03
Patent number
US08389766B2

Reaction notes

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