5-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-N-methyl-2-nitrobenzenesulfonamide → 2-amino-5-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-N-methylbenzenesulfonamide

HRID 77384Notes

Reaction equation

HRID 77384 reaction equation
[N:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[N:4]([C:10]1[CH:11]=[CH:12][C:13]([N+:21]([O-])=O)=[C:14]([S:16]([NH:19][CH3:20])(=[O:18])=[O:17])[CH:15]=1)[CH2:3][CH2:2]2.[H][H]>N.CO.[Pd]>[NH2:21][C:13]1[CH:12]=[CH:11][C:10]([N:4]2[CH:5]3[CH2:8][CH2:9][N:1]([CH2:7][CH2:6]3)[CH2:2][CH2:3]2)=[CH:15][C:14]=1[S:16]([NH:19][CH3:20])(=[O:17])=[O:18]

Participants

6

Reactant 2

HCID 671149585-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-N-methyl-2-nitrobenzenesulfonamide2×HCID 178418361HCID 178418361, compound

Product 1

HCID 671152852-amino-5-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-N-methylbenzenesulfonamideYield 95.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

5-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-N-methyl-2-nitrobenzenesulfonamide (Intermediate 17A) (1.0 g, 2.94 mmol) was dissolved in 2M ammonia in methanol (110 mL). The resulting solution was hydrogenated using the H-cube at 40° C. under 30 bar pressure of hydrogen, with a flow rate of 1 mL per minute through a 10% palladium on charcoal cartridge. The reaction mixture was purified by SCX and evaporated to afford 2-amino-5-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-N-methylbenzenesulfonamide, (868 mg, 2.8 mmol). 1H NMR; δ (ppm)(CHCl3-d): 7.17 (1H, d, J=3.01 Hz), 6.88 (1H, dd, J=9.04, 3.01 Hz), 6.72 (1H, d, J=9.04 Hz), 4.82 (1H, bs), 4.31 (2H, bs), 3.88-3.87 (1H, m), 3.42-3.39 (2H, m), 3.13-2.97 (6H, m), 2.57 (3H, d, J=3.51 Hz), 2.11-2.04 (2H, m), 1.76-1.68 (2H, m).

Workup

  1. customat 40° C.
  2. customThe reaction mixture was purified by SCX
  3. customevaporated

Sources & evidence

ORD record
ord-2d2672068bd94e5ca496ae5e6b7ff508
Source dataset
uspto-grants-2014_09
Patent number
US08841289B2

Reaction notes

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