Methylamine → 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-N-methyl-5-nitroisonicotinamide

HRID 77393Notes

Reaction equation

HRID 77393 reaction equation
[N:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[N:4]([C:10]1[CH:11]=[C:12]([C:17]([N+:20]([O-:22])=[O:21])=[CH:18][N:19]=1)[C:13]([O:15]C)=O)[CH2:3][CH2:2]2.[CH3:23][NH2:24]>CO>[N:1]12[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9]1)[N:4]([C:10]1[CH:11]=[C:12]([C:17]([N+:20]([O-:22])=[O:21])=[CH:18][N:19]=1)[C:13]([NH:24][CH3:23])=[O:15])[CH2:3][CH2:2]2

Participants

4

Reactant 2

HCID 6329MethylamineHCID 67114669Methyl 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)5-nitroisonicotinate2×

Product 1

HCID 671149702-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-N-methyl-5-nitroisonicotinamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

Methyl 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)5-nitroisonicotinate (Intermediate 27A) (0.1 g, 0.46 mmol) and 2M methylamine in methanol (5 mL) were sealed in a tube and heated at 90° C. overnight. The reaction mixture was concentrated and purified by a 10 g silica column eluting with 0-10% methanol in DCM to afford 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-N-methyl-5-nitroisonicotinamide (96 mg, 0.31 mmol).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by a 10 g silica column
  3. washeluting with 0-10% methanol in DCM

Sources & evidence

ORD record
ord-3e59eb3b3eb9406283bfe5156658b028
Source dataset
uspto-grants-2014_09
Patent number
US08841289B2

Reaction notes

Loading…