Methanesulfonyl chloride → N-(8-propyl-8-azabicyclo[3.2.1]oct-3-yl)-N-(1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-yl)-methanesulfonamide

HRID 1269886Notes

Reaction equation

HRID 1269886 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([N:9]1[CH:14]2[CH2:15][CH2:16][CH:10]1[CH2:11][CH:12]([NH:17][C:18]1[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=1)[N:23]([CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][O:28]1)[N:22]=[CH:21]3)[CH2:13]2)[CH2:7][CH3:8].C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[CH2:6]([N:9]1[CH:14]2[CH2:15][CH2:16][CH:10]1[CH2:11][CH:12]([N:17]([C:18]1[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=1)[N:23]([CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][O:28]1)[N:22]=[CH:21]3)[S:2]([CH3:1])(=[O:4])=[O:3])[CH2:13]2)[CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 18447446N-(8-propyl-8-azabicyclo[3.2.1]oct-3-yl)-1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-amine

Product 1

HCID 18447449N-(8-propyl-8-azabicyclo[3.2.1]oct-3-yl)-N-(1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-yl)-methanesulfonamideYield 44.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulfonyl chloride (0.10 ml, 1.29 mmol) was added to a solution of N-(8-propyl-8-azabicyclo[3.2.1]oct-3-yl)-1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-amine (37 mg, 0.100 mmol) in pyridine (1 ml), and the resulting mixture was stirred at room temperature for 3 days. The reaction solution was poured into a saturated aqueous sodium hydrogencarbonate solution, followed by extraction with ethyl acetate, and the extract solution was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, and then distilled under reduced pressure to remove the solvent. The residue was purified by a preparative thin-layer chromatography (200×200×0.5 mm, 2 plates, eluent: chloroform/methanol=20/1) to obtain N-(8-propyl-8-azabicyclo[3.2.1]oct-3-yl)-N-(1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-yl)-methanesulfonamide (20 mg, 44%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washthe extract solution was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customThe residue was purified by a preparative thin-layer chromatography (200×200×0.5 mm, 2 plates, eluent: chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-d7987ff21a594ca7b3c6861164791627
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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