tert-butyl-1-(4-(N-1,2,4-thiadiazol-5-ylsulfamoyl)phenyl)piperidin-4-ylcarbamate → 4-(4-aminopiperidin-1-yl)-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide

HRID 1696136Notes

Reaction equation

HRID 1696136 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([S:20](=[O:28])(=[O:27])[NH:21][C:22]3[S:26][N:25]=[CH:24][N:23]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)(C)(C)C>Cl.O1CCOCC1>[NH2:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([NH:21][C:22]3[S:26][N:25]=[CH:24][N:23]=3)(=[O:28])=[O:27])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1

Participants

3

Reactant 1

HCID 59465703tert-butyl-1-(4-(N-1,2,4-thiadiazol-5-ylsulfamoyl)phenyl)piperidin-4-ylcarbamate

Product 1

HCID 594657314-(4-aminopiperidin-1-yl)-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamideYield 81%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

Prepared using general procedure 28, method B. Under N2 atmosphere, a solution of tert-butyl-1-(4-(N-1,2,4-thiadiazol-5-ylsulfamoyl)phenyl)piperidin-4-ylcarbamate (3 g, 7.02 mmol) in 4 M HCl/dioxane (100 mL) was stirred at RT for 16 h. The formed precipitate was filtered off and washed with dioxane (20 mL) to give 4-(4-aminopiperidin-1-yl)-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide (1.88 g, 81%). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=340; tR=1.28 min.

Workup

  1. customPrepared
  2. filtrationThe formed precipitate was filtered off
  3. washwashed with dioxane (20 mL)

Sources & evidence

ORD record
ord-6803e821ba204fffbc437cf7f96ecb61
Source dataset
uspto-grants-2012_04
Patent number
US08163720B2

Reaction notes

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