Triethylamine → HCID 86620399, compound

HRID 252724Notes

Reaction equation

HRID 252724 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:17]([NH:20][C:21]1[S:22][C:23]([C:27]2[CH:28]=[C:29]([S:34](Cl)(=[O:36])=[O:35])[C:30]([Cl:33])=[N:31][CH:32]=2)=[C:24]([CH3:26])[N:25]=1)(=[O:19])[CH3:18]>C1COCC1>[Cl:33][C:30]1[N:31]=[CH:32][C:27]([C:23]2[S:22][C:21]([NH:20][C:17](=[O:19])[CH3:18])=[N:25][C:24]=2[CH3:26])=[CH:28][C:29]=1[S:34](=[O:35])(=[O:36])[NH:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 660364-ChlorobenzylamineHCID 86620400HCID 86620400, compound

Product 1

HCID 86620399HCID 86620399, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-Chlorobenzylamine (0.17 mL) and triethylamine (0.12 mL) were added in turn to a stirred slurry of 5-(2-acetamido-4-methyl-1,3-thiazol-5-yl)-2-chloropyridine-3-sulfonyl chloride (250 mg) in THF (20 mL) that had been cooled to 0° C. The resultant mixture was stirred at 0° C. for 30 minutes and at room temperature for 1 hour. The mixture was evaporated and the residue was partitioned between dichloromethane and water. The organic solution was washed with a saturated aqueous sodium chloride solution, filtered, dried over magnesium sulfate and evaporated. The material so obtained was purified by ‘basic reversed-phase chromatography’ (Waters ‘Xterra’ C18 reversed-phase silica, 150×21 mm, solvent gradient of 5-50% acetonitrile in water (containing 1% aqueous ammonium hydroxide (d=0.88) solution). The material so obtained was triturated under diethyl ether, isolated and dried at 55° C. under vacuum. There was thus obtained the title compound as a white solid (155 mg); 1H NMR Spectrum: (DMSOd6) 2.22 (s, 3H), 2.40 (s, 3H), 4.24 (s, 2H), 7.25 (s, 4H), 8.06 (m, 1H), 8.63 (m, 1H), 9.06 (br s, 1H), 12.54 (br s, 11H); Mass Spectrum: M+H+ 471 and 473.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was partitioned between dichloromethane and water
  3. washThe organic solution was washed with a saturated aqueous sodium chloride solution
  4. filtrationfiltered
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe material so obtained
  8. customwas purified by ‘basic reversed-phase chromatography’ (Waters ‘Xterra’ C18 reversed-phase silica, 150×21 mm, solvent gradient of 5-50% acetonitrile in water (containing 1% aqueous ammonium hydroxide (d=0.88) solution)
  9. customThe material so obtained
  10. customwas triturated under diethyl ether
  11. customisolated
  12. customdried at 55° C. under vacuum

Sources & evidence

ORD record
ord-f63dcc51352045298bfc75c8bb804a6b
Source dataset
uspto-grants-2011_01
Patent number
US07868188B2

Reaction notes

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