HCID 67115180, compound → 2-amino-5-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-N-(2-(isopropylamino)-2-oxoethyl)benzamide

HRID 77374Notes

Reaction equation

HRID 77374 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+:26]([O-])=O)=[C:14]([CH:25]=1)[C:15]([NH:17][CH2:18][C:19]([NH:21][CH:22]([CH3:24])[CH3:23])=[O:20])=[O:16])[CH2:3][CH2:2]2.[H][H]>CO.[Pd]>[NH2:26][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:25][C:14]=1[C:15]([NH:17][CH2:18][C:19]([NH:21][CH:22]([CH3:24])[CH3:23])=[O:20])=[O:16]

Participants

5

Reactant 2

HCID 67115180HCID 67115180, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 671150572-amino-5-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-N-(2-(isopropylamino)-2-oxoethyl)benzamideYield 98.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-N-(2-(isopropylamino)-2-oxoethyl)-2-nitrobenzamide (Intermediate 4A) (7.0 g, 18.0 mmol) was dissolved in methanol (120 mL) and palladium on carbon (0.7 g) added. The resulting solution was hydrogenated at room temperature under 4 bar pressure of hydrogen overnight. The reaction mixture was filtered through a celite pad, washed with methanol and dichloromethane, and concentrated to afford 2-amino-5-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-N-(2-(isopropylamino)-2-oxoethyl)benzamide (6.4 g, 17.8 mmol).

Workup

  1. filtrationThe reaction mixture was filtered through a celite pad
  2. washwashed with methanol and dichloromethane
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9558f119a62d4df286cd3ab11e817182
Source dataset
uspto-grants-2014_09
Patent number
US08841289B2

Reaction notes

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