Acetic Anhydride → HCID 59509042, compound

HRID 1020064Notes

Reaction equation

HRID 1020064 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([CH:18]2[CH2:23][CH2:22][CH2:21][NH:20][CH2:19]2)=[O:17])[CH:10]=1.[C:24](OC(=O)C)(=[O:26])[CH3:25]>ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([CH:18]2[CH2:23][CH2:22][CH2:21][N:20]([C:24](=[O:26])[CH3:25])[CH2:19]2)=[O:17])[CH:10]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 25227433HCID 25227433, compound

Product 1

HCID 59509042HCID 59509042, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Piperidine-3-carboxylic acid [6-(2-methoxy-phenyl)-pyrimidin-4-yl]amide (compound #16A) (110 mg, 0.352 mmol) was dissolved in 5 ml of anhydrous dichloromethane, cooled to 0° C. and 4-N,N-dimethylaminopyridine (90 mg, 0.70 mmol) and acetic anhydride (54 mg, 0.53 mmol) were added simultaneously. The reaction mixture was stirred for 3 hours at room temperature, treated with crushed ice and partitioned between water and dichloromethane. The organic layer was separated, dried over sodium sulfate and concentrated to provide 1-acetyl-piperidine-3-carboxylic acid [6-(2-methoxy-phenyl)-pyrimidin-4-yl]-amide (compound #20A) (105 mg, 84.13%).

Workup

  1. additiontreated with crushed ice
  2. custompartitioned between water and dichloromethane
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-175f03cfe447420bb259d26a5b57b665
Source dataset
uspto-grants-2014_05
Patent number
US08716296B2

Reaction notes

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