Acryloyl chloride → HCID 86724360, compound

HRID 1482707Notes

Reaction equation

HRID 1482707 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][OH:23])[CH:17]=2)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[C:5]([F:24])=[CH:4][N:3]=1.[C:25](Cl)(=[O:28])[CH:26]=[CH2:27].CCCCCC.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>O>[Cl:1][C:2]1[N:7]=[C:6]([N:8]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N:22]([OH:23])[C:25](=[O:28])[CH:26]=[CH2:27])[CH:17]=2)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[C:5]([F:24])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 13140Acryloyl chlorideHCID 516892Sodium BicarbonateHCID 21226206Ethyl acetate hexaneHCID 86724359HCID 86724359, compound

Product 1

HCID 86724360HCID 86724360, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-40 °C

Procedure

In a 25 ml 3-neck RBF was equipped with a magnetic stirrer and CaCl2 guard tube was added tert-butyl (2-chloro-5-fluoropyrimidin-4-yl)(3-(hydroxyamino)phenyl)carbamate (0.409 g in 5 ml DCM). The reaction was cooled to −40° C. and acryloyl chloride (0.114 g in 3 ml DCM) was slowly added. The reaction mixture was warmed to room temperature and stirred at room temperature for 30 min. The reaction was monitored on TLC using hexane:ethyl acetate (7:3) as mobile phase. The reaction was complete after 30 min and was poured in water (100 ml) and basified using sodium bicarbonate solution. The reaction mixture was extracted with DCM (2×25 ml) and the combined organic layer was washed with brine solution, dried over sodium sulfate and concentrated completely under reduced pressure at 40° C. Crude material was purified by using column chromatography. Product was eluted with 14% ethyl acetate in hexane to give, after concentration, 0.250 g of tert-butyl (2-chloro-5-fluoropyrimidin-4-yl)(3-(N-hydroxyacrylamido)phenyl)carbamate

Workup

  1. customIn a 25 ml 3-neck RBF was equipped with a magnetic stirrer and CaCl2 guard tube
  2. temperatureThe reaction mixture was warmed to room temperature
  3. waitThe reaction was complete after 30 min
  4. extractionThe reaction mixture was extracted with DCM (2×25 ml)
  5. washthe combined organic layer was washed with brine solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated completely under reduced pressure at 40° C
  8. customCrude material was purified
  9. washProduct was eluted with 14% ethyl acetate in hexane
  10. customto give
  11. concentrationafter concentration, 0.250 g of tert-butyl (2-chloro-5-fluoropyrimidin-4-yl)(3-(N-hydroxyacrylamido)phenyl)carbamate

Sources & evidence

ORD record
ord-da4b0ffdb35d4f90a5bba8b38f2c1b4c
Source dataset
uspto-grants-2016_08
Patent number
US09415049B2

Reaction notes

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