Acetyl chloride → HCID 58169356, compound

HRID 1484998Notes

Reaction equation

HRID 1484998 reaction equation
[Br:1][C:2]1[C:3]([NH:10][C:11]2[C:16]([Cl:17])=[CH:15][N:14]=[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH:24]([OH:27])[CH:25]=[CH2:26])[N:12]=2)=[N:4][NH:5][C:6]=1[CH:7]1[CH2:9][CH2:8]1.[C:28](Cl)(=[O:30])[CH3:29]>C1COCC1>[Br:1][C:2]1[C:3]([NH:10][C:11]2[C:16]([Cl:17])=[CH:15][N:14]=[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH:24]([OH:27])[CH:25]=[CH2:26])[N:12]=2)=[N:4][N:5]([C:28](=[O:30])[CH3:29])[C:6]=1[CH:7]1[CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 58169347HCID 58169347, compound

Product 1

HCID 58169356HCID 58169356, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of 1-(2-(4-(4-bromo-5-cyclopropyl-1H-pyrazol-3-ylamino)-5-chloropyrimidin-2-yl)phenyl)prop-2-en-1-ol (550 mg, 1.2 mmol, 1.0 eq) in THF (20 mL), a solution of acetyl chloride (966 mg, 12 mmol, 10 eq) in THF (2 mL) was added. The mixture was stirred at 0° C. for 4 h, then, partitioned between EtOAc and water. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to provide 1-(4-bromo-3-(5-chloro-2-(2-(1-hydroxyallyl)phenyl)pyrimidin-4-ylamino)-5-cyclopropyl-1H-pyrazol-1-yl)ethanone (310 mg, 52%). LC-MS (m/z)=488.0, 490.0 [M+H]+.

Workup

  1. custompartitioned between EtOAc and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-8036c6ea7633427091a3062c819cb68e
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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