HCID 59253395, compound → HCID 86640292, compound

HRID 1258546Notes

Reaction equation

HRID 1258546 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:18]#[N:19])=[C:6]([NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH:7]=1.[CH3:20][C:21]1[CH:29]=[C:28]([C:30]([F:39])([C:35]([F:38])([F:37])[F:36])[C:31]([F:34])([F:33])[F:32])[CH:27]=[C:26]([CH3:40])[C:22]=1[C:23](Cl)=[O:24]>O1CCCC1.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[C:18]([C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:23](=[O:24])[C:22]2[C:21]([CH3:20])=[CH:29][C:28]([C:30]([F:39])([C:31]([F:32])([F:33])[F:34])[C:35]([F:36])([F:37])[F:38])=[CH:27][C:26]=2[CH3:40])=[CH:7][C:6]=1[NH:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)#[N:19]

Participants

6

Reactant 2

HCID 59253395HCID 59253395, compoundHCID 68526880HCID 68526880, compound

Product 1

HCID 86640292HCID 86640292, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of N-(5-amino-2-cyano-phenyl)-4-fluoro-benzamide (0.20 g, 0.78 mmol) (Example I9) in anhydrous tetrahydrofuran (2.5 ml) under an atmosphere of nitrogen was added at room temperature a solution of 2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-benzoyl chloride (0.332 g, 1.04 mmol) (Example I4) in anhydrous tetrahydrofuran (2.5 ml). The reaction mixture was stirred at room temperature for 48 hours. The reaction mixture was diluted with ethyl acetate and aqueous sodium hydrogen carbonate (saturated). The phases were separated and the aqueous phase was extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 3:1) to give N-[4-cyano-3-(4-fluoro-benzoylamino)-phenyl]-2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-benzamide (131 mg, 66% yield). 1H-NMR (CDCl3, 400 MHz): 8.98 (s, 1H), 8.51 (d, 1H), 8.45 (s, 1H), 8.33 (s, 1H), 8.21 (dd, 1H), 7.84 (m, 2H), 7.68 (d, 1H), 7.34 (s, 1H), 6.78 (t, 2H) ppm.

Workup

  1. customwas added at room temperature
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted twice with ethyl acetate
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-c4b1dd3ea25e4a429001081da6a1a179
Source dataset
uspto-grants-2013_06
Patent number
US08466180B2

Reaction notes

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