Acetyl chloride → N-{4-[2-(1-Acetylpiperidin-4-yl)-4-(3-chlorophenyl)-1,3-thiazol-5-yl]pyridin-2-yl}acetamide

HRID 1727376Notes

Reaction equation

HRID 1727376 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:5]=[C:6]([C:10]2[N:11]=[C:12]([CH:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)[S:13][C:14]=2[C:15]2[CH:20]=[CH:19][N:18]=[C:17]([NH:21][C:22](=[O:24])[CH3:23])[CH:16]=2)[CH:7]=[CH:8][CH:9]=1.[C:31](Cl)(=[O:33])[CH3:32].C(N(CC)CC)C.C(=O)([O-])O.[Na+]>O1CCCC1>[C:31]([N:28]1[CH2:29][CH2:30][CH:25]([C:12]2[S:13][C:14]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH:21][C:22](=[O:24])[CH3:23])[CH:16]=3)=[C:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([Cl:3])[CH:5]=3)[N:11]=2)[CH2:26][CH2:27]1)(=[O:33])[CH3:32]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 68827428HCID 68827428, compound

Product 1

HCID 53432114N-{4-[2-(1-Acetylpiperidin-4-yl)-4-(3-chlorophenyl)-1,3-thiazol-5-yl]pyridin-2-yl}acetamideYield 62.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of N-[4-[4-(3-chlorophenyl)-2-(4-piperidyl)-1,3-thiazol-5-yl]-2-pyridyl]acetamide dihydrochloride (0.41 g, 0.84 mmol) in tetrahydrofuran (20 mL) were added acetyl chloride (0.13 mL, 1.8 mmol) and triethylamine (0.50 mL, 3.6 mmol) sequentially, and the resulting mixture was stirred at room temperature for 30 minutes. Aqueous sodium hydrogen carbonate was added to the reaction mixture and extracted with ethyl acetate. The extracts were washed with water, dried, and concentrated. The residue was recrystallized from ethyl acetate-hexane to give a title compound (0.24 g, yield 62%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-5d4a3c857a14419aadb13845da5bb725
Source dataset
uspto-grants-2009_02
Patent number
US07495018B2

Reaction notes

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