Sulfamide → HCID 22031401, compound

HRID 1792548Notes

Reaction equation

HRID 1792548 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[N:13]=[CH:12][CH:11]=[C:10]3[N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[CH:5][N:4]([C:23]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:3]=1.[S:42](N)([NH2:45])(=[O:44])=[O:43]>O1CCOCC1>[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[N:13]=[CH:12][CH:11]=[C:10]3[N:17]2[CH:18]=[CH:19][N:20]([S:42]([NH2:45])(=[O:44])=[O:43])[CH:21]=[CH:22]2)=[CH:5][N:4]([C:23]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:3]=1

Participants

4

Reactant 2

HCID 82267SulfamideHCID 22031305HCID 22031305, compound

Product 1

HCID 22031401HCID 22031401, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 54 mg 6-(3-methyl-1-trityl-1H-4-pyrazolyl)-4-piperazin-1-yl-quinoline obtained in Example 187, 96 mg sulfamide, and 5 mL dioxane was heated for 4 hours under reflux. The reaction solution was evaporated, then ethyl acetate and water were added to the residue, and the organic layer was separated, then washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give 45 mg of the title compound as a white solid.

Workup

  1. temperaturewas heated for 4 hours
  2. temperatureunder reflux
  3. customThe reaction solution was evaporated
  4. additionethyl acetate and water were added to the residue
  5. customthe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated
  9. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-83099ed2ec08478b8244911b8743b6fd
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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