Pyridine → HCID 59497818, compound

HRID 1917057Notes

Reaction equation

HRID 1917057 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][CH:32]=1)[C:5]([NH:7][C:8]1[C:13]([Br:14])=[CH:12][C:11]([C:15]([C:21]2[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=2)([OH:20])[C:16]([F:19])([F:18])[F:17])=[CH:10][C:9]=1[Br:29])=[O:6].N1C=CC=CC=1.[C:39]([C:41]1[CH:49]=[CH:48][C:44]([C:45](Cl)=[O:46])=[CH:43][CH:42]=1)#[N:40].C(=O)([O-])O.[Na+]>O1CCCC1>[C:39]([C:41]1[CH:49]=[CH:48][C:44]([C:45]([NH:1][C:2]2[CH:3]=[C:4]([CH:30]=[CH:31][CH:32]=2)[C:5]([NH:7][C:8]2[C:9]([Br:29])=[CH:10][C:11]([C:15]([C:21]3[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=3)([OH:20])[C:16]([F:19])([F:17])[F:18])=[CH:12][C:13]=2[Br:14])=[O:6])=[O:46])=[CH:43][CH:42]=1)#[N:40]

Participants

6

Reactant 4

HCID 1049PyridineHCID 801724-Cyanobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 59497828HCID 59497828, compound

Product 1

HCID 59497818HCID 59497818, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-amino-N-{2,6-dibromo-4-[1-(3,5-dichloro-phenyl)-2,2,2-trifluoro-1-hydroxy-ethyl]-phenyl}-benzamide (Example I8) (0.147 mg, 0.24 mmol) in tetrahydrofuran (5 ml) were added successively pyridine (0.058 ml, 0.72 mmol) and 4-cyano-benzoyl chloride (48 mg, 0.29 mmol). The reaction mixture was stirred at ambient temperature for 2 hours. 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 1:1) to give the title compound.

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 1:1)

Sources & evidence

ORD record
ord-f3a25badd5ce44b997e28d9b2ddfadc9
Source dataset
uspto-grants-2013_12
Patent number
US08618173B2

Reaction notes

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