Sodium Sulfate → HCID 86680416, compound

HRID 1023174Notes

Reaction equation

HRID 1023174 reaction equation
[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7](/[CH:12]=[CH:13]/[C:14]([OH:16])=O)[CH:8]=2)[N:3]1COCC[Si](C)(C)C.[CH3:25]N(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:49][CH:50]([F:64])[O:51][C:52]1[CH:57]=[CH:56][C:55]([NH:58]/[C:59](/[NH2:62])=[N:60]/O)=[C:54](C)[CH:53]=1.S([O-])([O-])(=O)=O.[Na+].[Na+]>CN(C=O)C.O>[F:64][CH:50]([F:49])[O:51][C:52]1[CH:53]=[CH:54][C:55]([NH:58][C:59]2[N:60]=[C:14](/[CH:13]=[CH:12]/[C:7]3[CH:8]=[C:9]4[C:4](=[CH:5][CH:6]=3)[NH:3][C:2](=[O:1])[CH:11]=[CH:10]4)[O:16][N:62]=2)=[CH:56][C:57]=1[CH3:25]

Participants

7

Reactant 4

HCID 24436Sodium SulfateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86680417HCID 86680417, compoundHCID 178429108HCID 178429108, compound

Product 1

HCID 86680416HCID 86680416, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
90 °C

Procedure

To a solution of (E)-3-(2-oxo-1-((2-(trimethylsilyl)ethoxy)methyl)-1,2-dihydroquinolin-6-yl)acrylic acid (80 mg, 0.232 mmol) and HATU (132 mg, 0.347 mmol) in DMF (2 ml) was added TEA (0.097 mL, 0.695 mmol). The reaction mixture was stirred for 30 minutes. A solution of (E)-1-(4-(difluoromethoxy)-2-methylphenyl)-2-hydroxyguanidine (80 mg, 0.347 mmol) in DMF was then added to and stirred at room temperature for 1 h. Sodium sulfate (99 mg, 0.695 mmol) was added and the reaction mixture was heated at 90° C. overnight. Water was added and the mixture was extracted with ethyl acetate (2×50 mL). The organic layer was dried over sodium sulfate and concentrated. The crude product was purified by flash chromatography on silica gel using 10-12% chloroform in ethyl acetate to obtain (E)-6-(2-(3-((4-(difluoromethoxy)-3-methylphenyl)amino)-1,2,4-oxadiazol-5-yl)vinyl)quinolin-2(1H)-one (65 mg, 52%). LCMS, RT 2.298 min; LCMS (ES-API), m/z 541.

Workup

  1. stirringstirred at room temperature for 1 h
  2. extractionthe mixture was extracted with ethyl acetate (2×50 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography on silica gel using 10-12% chloroform in ethyl acetate

Sources & evidence

ORD record
ord-e863b7110662462fb35cf2fb99d8058b
Source dataset
uspto-grants-2014_05
Patent number
US08722670B2

Reaction notes

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