Acetyl chloride → HCID 25099824, compound

HRID 2381983Notes

Reaction equation

HRID 2381983 reaction equation
Cl.Cl.[N:3]1([NH:9][C:10]([C:12]2[CH:13]=[N:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:16][CH:17]=2)=[O:11])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[C:24](Cl)(=[O:26])[CH3:25].CCN(CC)CC>CN(C=O)C>[C:24]([N:6]1[CH2:5][CH2:4][N:3]([NH:9][C:10]([C:12]2[CH:17]=[N:16][C:15]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[N:14][CH:13]=2)=[O:11])[CH2:8][CH2:7]1)(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 68553079HCID 68553079, compound

Product 1

HCID 25099824HCID 25099824, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-phenyl-pyrimidine-5-carboxylic acid piperazin-1-ylamide dihydrochloride (0.43 mmol), acetyl chloride (1.28 mmol) and Et3N (1.72 mmol) in DMF (8 mL) is stirred at rt overnight. mixture is concentrated in vacuo. The residue is dissolved in EtOAc (15 mL), washed with water and brine, dried (Na2SO4), filtered and concentrated in vacuo. The residue is triturated with ether to afford 2-phenyl-pyrimidine-5-carboxylic acid (4-acetyl-piperazin-1-yl)-amide (98 mg, 71%) as a solid. MS: 326 (M+H); 1H NMR (300 MHz, CDCl3): δ 2.12 (s, 3H), 2.92-3.10 (m, 4H), 3.40-4.10 (m, 4H), 7.43-7.60 (m, 3H), 7.75 (br, N—H), 8.52 (m, 2H), 9.11-9.38 (br, 2H).

Workup

  1. concentrationmixture is concentrated in vacuo
  2. dissolutionThe residue is dissolved in EtOAc (15 mL)
  3. washwashed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is triturated with ether

Sources & evidence

ORD record
ord-9850984cc4634349abddab85c030af43
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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