Triethylamine → 3-(8-Azabicyclo[3.2.1]octan-8-yl)sulfonyl-1-dimethylcarbamoyl-1H-1,2,4-triazole

HRID 1293148Notes

Reaction equation

HRID 1293148 reaction equation
Cl[S:2]([C:5]1[N:9]=[CH:8][N:7]([C:10](=[O:14])[N:11]([CH3:13])[CH3:12])[N:6]=1)(=[O:4])=[O:3].Cl.[CH:16]12[NH:23][CH:20]([CH2:21][CH2:22]1)[CH2:19][CH2:18][CH2:17]2.C(N(CC)CC)C>C(OCC)(=O)C>[CH:20]12[N:23]([S:2]([C:5]3[N:9]=[CH:8][N:7]([C:10](=[O:14])[N:11]([CH3:13])[CH3:12])[N:6]=3)(=[O:4])=[O:3])[CH:16]([CH2:22][CH2:21]1)[CH2:17][CH2:18][CH2:19]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5222728-Azabicyclo[3.2.1]octane hydrochlorideHCID 178387483-chlorosulfonyl-1-dimethylcarbamoyl-1H-1,2,4-triazole

Product 1

HCID 589054543-(8-Azabicyclo[3.2.1]octan-8-yl)sulfonyl-1-dimethylcarbamoyl-1H-1,2,4-triazoleYield 24.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-chlorosulfonyl-1-dimethylcarbamoyl-1H-1,2,4-triazole (Example 54-a) (470 mg), 8-azabicyclo[3.2.1]octane hydrochloride (350 mg), triethylamine (0.7 ml), and ethyl acetate (10 ml) was stirred overnight at room temperature. The reaction solution was washed with water, followed by saturated aqueous sodium chloride solution, and concentrated. The residue was subjected to a silica-gel column chromatography with 50 to 100% ethyl acetate/hexane to yield the title compound (150 mg).

Workup

  1. washThe reaction solution was washed with water
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-808be267f9064c308abe3a533da335b4
Source dataset
uspto-grants-2007_07
Patent number
US07238720B2

Reaction notes

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