Sodium hydride → HCID 86665282, compound

HRID 1970843Notes

Reaction equation

HRID 1970843 reaction equation
[NH2:1][C:2]1[C:3]([F:34])=[C:4]([CH:29]=[CH:30][C:31]=1[C:32]#[N:33])[C:5]([NH:7][C:8]1[C:13]([Cl:14])=[CH:12][C:11]([C:15]([F:27])([C:23]([F:26])([F:25])[F:24])[C:16]([F:22])([F:21])[C:17]([F:20])([F:19])[F:18])=[CH:10][C:9]=1[Cl:28])=[O:6].[H-].[Na+].C(C1C=CC(C(NC2C(Br)=CC(C(F)(C(F)(F)F)C(F)(F)C(F)(F)F)=CC=2Br)=O)=CC=1N[C:70](=[O:80])[C:71]1[CH:76]=[CH:75][C:74]([C:77]#[N:78])=[CH:73][C:72]=1[CH3:79])#N.C(=O)([O-])O.[Na+]>CN(C)C(=O)C>[C:32]([C:31]1[CH:30]=[CH:29][C:4]([C:5]([NH:7][C:8]2[C:9]([Cl:28])=[CH:10][C:11]([C:15]([F:27])([C:23]([F:24])([F:25])[F:26])[C:16]([F:21])([F:22])[C:17]([F:18])([F:19])[F:20])=[CH:12][C:13]=2[Cl:14])=[O:6])=[C:3]([F:34])[C:2]=1[NH:1][C:70](=[O:80])[C:71]1[CH:76]=[CH:75][C:74]([C:77]#[N:78])=[CH:73][C:72]=1[CH3:79])#[N:33]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 46944255HCID 46944255, compoundHCID 86665283HCID 86665283, compound

Product 1

HCID 86665282HCID 86665282, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a suspension of 3-amino-4-cyano-N-[2,6-dichloro-4-(1,2,2,3,3,3-hexafluoro-1-trifluoromethylpropyl)phenyl]-2-fluorobenzamide (Example 1.7) (0.054 g, 0.10 mmol) in N,N-dimethylacetamide (“DMA”) (1 ml) was added sodium hydride (55% w/v) (0.018 g, 0.40 mmol). The reaction mixture was stirred for 30 minutes at ambient temperature and then 4-cyano-2-methylbenzoyl chloride (see first part of Example 2.1) (0.10 mmol) was added. The reaction mixture was stirred at ambient temperature for 16 hours. Satruated aqueous sodium hydrogen carbonate (30 ml) was added and the organic phase extracted twice with ethyl acetate (2×20 ml). 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 7:3) to give Compound No. A18 of Table A (0.010 g, 15% yield).

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for 16 hours
  2. extractionthe organic phase extracted twice with ethyl acetate (2×20 ml)
  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 7:3)
  6. customto give Compound No

Sources & evidence

ORD record
ord-9013733cbdf64ba28b56614be6d4cad9
Source dataset
uspto-grants-2013_04
Patent number
US08431514B2

Reaction notes

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