Acetyl chloride → HCID 58423313, compound

HRID 1398009Notes

Reaction equation

HRID 1398009 reaction equation
[N:1]1([C:7]2[CH:20]=[CH:19][CH:18]=[CH:17][C:8]=2/[CH:9]=[C:10]2/[C:11](=[O:16])[NH:12][C:13](=[O:15])[S:14]/2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:21](Cl)(=[O:23])[CH3:22].C(N(CC)CC)C.C([O-])(O)=O.[Na+]>>[C:21]([N:4]1[CH2:5][CH2:6][N:1]([C:7]2[CH:20]=[CH:19][CH:18]=[CH:17][C:8]=2/[CH:9]=[C:10]2/[C:11](=[O:16])[NH:12][C:13](=[O:15])[S:14]/2)[CH2:2][CH2:3]1)(=[O:23])[CH3:22]

Participants

5

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 58423155HCID 58423155, compound

Product 1

HCID 58423313HCID 58423313, compoundYield 35.4%

Procedure

To a mixture of (5Z)-5-(2-piperazin-1-ylbenzylidene)-1,3-thiazolidine-2,4-dione (Example 115) and acetyl chloride (36.1 mg, 0.46 mmol) was added triethylamine (93 mg, 0.92 mmol) at room temperature. The reaction mixture was stirred at room temperature overnight and was then treated with sat'd aqueous NaHCO3 (˜25 mL). This mixture was allowed to stir at room temperature for 10 min, and was then extracted with DCM (3×25 mL). The combined organic extract was dried over anhydrous Na2SO4, filtered through a bed of Celite, and the filtrate was conc. in vacuo to afford the product which was purified via reverse phase HPLC (acetonitrile:water: 0.1% TFA=5% to 70%) to afford the title compound as a pale yellow solid (40.0 mg, 35.4%). 1H NMR (300 MHz, DMSO-D6) δ ppm 12.58 (brs, 1 H) 7.94 (s, 1 H) 7.47 (d, 2 H) 7.30-7.07 (m, 2 H) 3.60 (brs, 4 H) 2.90 (brs, 2 H) 2.85 (brs, 2 H) 2.04 (s, 3 H); m/z 331.

Workup

  1. stirringto stir at room temperature for 10 min
  2. extractionwas then extracted with DCM (3×25 mL)
  3. extractionThe combined organic extract
  4. dry with materialwas dried over anhydrous Na2SO4
  5. filtrationfiltered through a bed of Celite
  6. customto afford the product which
  7. customwas purified via reverse phase HPLC (acetonitrile:water: 0.1% TFA=5% to 70%)

Sources & evidence

ORD record
ord-160ccc80e11d490d87e240a58e7b7561
Source dataset
uspto-grants-2014_12
Patent number
US08901307B2

Reaction notes

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