Benzenesulfonyl chloride → HCID 86620415, compound

HRID 252738Notes

Reaction equation

HRID 252738 reaction equation
C[Si](C)(C)N[Si](C)(C)C.[Li].[NH2:11][C:12]1[CH:13]=[C:14]([C:19]2[S:23][C:22]([NH:24][C:25](=[O:27])[CH3:26])=[N:21][C:20]=2[CH3:28])[N:15]=[N:16][C:17]=1[Cl:18].[C:29]1([S:35](Cl)(=[O:37])=[O:36])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O.C1COCC1>[CH3:28][C:20]1[N:21]=[C:22]([NH:24][C:25](=[O:27])[CH3:26])[S:23][C:19]=1[C:14]1[N:15]=[N:16][C:17]([Cl:18])=[C:12]([NH:11][S:35]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)(=[O:37])=[O:36])[CH:13]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 57426343Lithium bis(trimethylsilyl)amideHCID 86244451HCID 86244451, compound

Product 1

HCID 86620415HCID 86620415, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Lithium hexamethyldisilazane (1M solution in THF; 0.81 mL) was added to a mixture of N-[5-(5-amino-6-chloropyridazin-3-yl)-4-methyl-1,3-thiazol-2-yl]acetamide (77 mg) and THF (1.3 mL) that had been cooled to 0° C. The reaction mixture was allowed to warm and was stirred at room temperature for 30 minutes. Benzenesulfonyl chloride (0.069 mL) was added and the reaction mixture was stirred at room temperature for 2 hours. Water (2 drops) was added to the reaction mixture. The mixture was evaporated and the residual solid was purified by preparative HPLC. The material so obtained was purified further by column chromatography on silica using a solvent gradient of 0% to 20% methanol in dichloromethane as eluent. There was thus obtained the title compound as a solid (2.5 mg); 1H NMR Spectrum: (DMSOd6) 2.15 (s, 3H), 2.40 (s, 3H), 7.05 (s, 1H), 7.45 (m, 3H), 7.80 (m, 2H); Mass Spectrum: M+H+ 424.

Workup

  1. temperatureto warm
  2. stirringthe reaction mixture was stirred at room temperature for 2 hours
  3. customThe mixture was evaporated
  4. customthe residual solid was purified by preparative HPLC
  5. customThe material so obtained
  6. customwas purified further by column chromatography on silica using a solvent gradient of 0% to 20% methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-e17a838fe86944ac96de3f340fb579c0
Source dataset
uspto-grants-2011_01
Patent number
US07868188B2

Reaction notes

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