Sodium Acetate → HCID 86636265, compound

HRID 541796Notes

Reaction equation

HRID 541796 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[C:10]2[CH:24]=[C:23]([NH:25][C:26]3[C:31]([Cl:32])=[CH:30][N:29]=[C:28]([Cl:33])[N:27]=3)[CH:22]=[CH:21][C:11]=2[CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:5]=[N:6][CH:7]=1.C([O-])(=O)C.[Na+]>C1COCC1.O.C(OCC)(=O)C>[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]2[CH:24]=[C:23]([NH:25][C:26]3[C:31]([Cl:32])=[CH:30][N:29]=[C:28]([Cl:33])[N:27]=3)[CH:22]=[CH:21][C:11]=2[CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 2

HCID 517045Sodium Acetate2×HCID 86636266HCID 86636266, compound

Product 1

HCID 86636265HCID 86636265, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of tert-butyl {2-[(E)-2-(5-aminopyridin-3-yl)vinyl]-4-[(2,5-dichloropyrimidin-4-yl)amino]benzyl}carbamate (90.0 mg, 0.185 mmol) in THF (4 mL) was added p-toluenesulfonylhydrazide (0.515 g, 2.76 mmol). The reaction solution was heated to reflux at 90° C., then a solution of sodium acetate (0.363 g, 4.42 mmol) in water (3.7 mL, 20 mmol) was added dropwise over 4 h period. Another portion of p-toluenesulfonylhydrazide (0.343 g, 1.84 mmol) was added to reaction flask, then a solution of sodium acetate (0.242 g, 2.95 mmol) in water was added dropwise overnight under reflux. The reaction solution was diluted with ethyl acetate. Aqueous layer was extracted with ethyl acetate twice. The combined organic solutions were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography to yield the desired product (56 mg, 62%). LCMS for C24H29Cl2N6O2 (M+H)+: m/z=503.3, 505.3.

Workup

  1. temperatureThe reaction solution was heated
  2. temperatureunder reflux
  3. extractionAqueous layer was extracted with ethyl acetate twice
  4. washThe combined organic solutions were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-98b7ea13f0a240f4a9a28377b9923471
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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