Chlorosulfamic acid → HCID 23155691, compound

HRID 1714799Notes

Reaction equation

HRID 1714799 reaction equation
O[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[N:12]2[CH2:17][CH2:16][N:15]3[CH2:18][CH2:19][CH2:20][CH2:21][CH:14]3[CH2:13]2)=[CH:4][CH:3]=1.[S:22](Cl)(=[O:25])(=[O:24])[NH2:23].C(=O)([O-])O.[Na+]>CN1CCCC1=O>[CH2:13]1[N:12]([C:9]2[C:10]3[C:5](=[CH:4][CH:3]=[C:2]([S:22](=[O:25])(=[O:24])[NH2:23])[CH:11]=3)[CH:6]=[CH:7][N:8]=2)[CH2:17][CH2:16][N:15]2[CH2:18][CH2:19][CH2:20][CH2:21][CH:14]12

Participants

5

Reactant 3

HCID 24499Chlorosulfamic acidHCID 516892Sodium BicarbonateHCID 23155641HCID 23155641, compound

Product 1

HCID 23155691HCID 23155691, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

In 3 ml of N-methylpyrrolidone, 105 mg of 7-hydroxy-1-octahydropyrido[1,2-a]pyrazin-2-ylisoquinoline as synthesized in Production Example 84 was dissolved, and to the solution 1.00 g of sulfamoyl chloride was added, followed by an hour's stirring at room temperature. The solution was neutralized with saturated aqueous sodium hydrogencarbonate solution, extracted with chloroform, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified on silica gel column chromatography (25% aqueous ammonia:methanol:chloroform=1:10:90) to provide 85 mg (75%) of 1-octahydropyrido[1,2-a]pyrazin-2-yl-7-sulfamoylisoquinoline.

Workup

  1. dissolutionwas dissolved
  2. waitfollowed by an hour
  3. extractionextracted with chloroform
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified on silica gel column chromatography (25% aqueous ammonia:methanol:chloroform=1:10:90)

Sources & evidence

ORD record
ord-82bca172f51e425f95d7354f4cbed2d7
Source dataset
uspto-grants-2010_09
Patent number
US07799775B2

Reaction notes

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