Hydrochloric Acid → 2-Acetoxy-5-bromo-N-{4-[(1,1-dimethyl)ethyl)-5-piperidinothiazol-2-yl}benzamide

HRID 644441Notes

Reaction equation

HRID 644441 reaction equation
P(Cl)(Cl)(Cl)=O.[C:6]([O:9][C:10]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:11]=1[C:12]([OH:14])=O)(=[O:8])[CH3:7].[NH2:20][C:21]1[S:22][C:23]([N:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)=[C:24]([C:26]([CH3:29])([CH3:28])[CH3:27])[N:25]=1.Cl>O1CCCC1.N1C=CC=CC=1>[C:6]([O:9][C:10]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:11]=1[C:12]([NH:20][C:21]1[S:22][C:23]([N:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)=[C:24]([C:26]([CH3:29])([CH3:27])[CH3:28])[N:25]=1)=[O:14])(=[O:8])[CH3:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 739225-Bromo-2-acetylsalicylic acidHCID 858234922-Amino-4-[(1,1-dimethyl)ethyl]-5-piperidinothiazole

Product 1

HCID 866026812-Acetoxy-5-bromo-N-{4-[(1,1-dimethyl)ethyl)-5-piperidinothiazol-2-yl}benzamideYield 51.6%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under argon atmosphere, phosphorus oxychloride (46 μl, 0.50 mmol) was added to a mixture of 2-acetoxy-5-bromobenzoic acid (90.3 mg, 0.35 mmol), 2-amino-4-[(1,1-dimethyl)ethyl]-5-piperidinothiazole (80.7 mg, 0.34 mmol), pyridine (0.1 mL) and tetrahydrofuran (3 mL), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into 2N hydrochloric acid and extracted with ethyl acetate. After the organic layer was washed with water and brine, dried over anhydrous sodium sulfate, the residue obtained by evaporation under reduced pressure was purified by chromatography on silica gel (n-hexane:ethyl acetate=3:1) to give the title compound (84.3 mg) as a crude product.

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter the organic layer was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe residue obtained by evaporation under reduced pressure
  5. customwas purified by chromatography on silica gel (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-b96fdc81fcec48e99a12c3cef1141f15
Source dataset
uspto-grants-2010_04
Patent number
US07700655B2

Reaction notes

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