6530-09-2 → HCID 67115295, compound

HRID 77373Notes

Reaction equation

HRID 77373 reaction equation
Cl.[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH:4]([NH2:10])[CH2:3]2.CN1CCCN(C)P1.F[C:20]1[CH:21]=[CH:22][C:23]([N+:30]([O-:32])=[O:31])=[C:24]([CH:29]=1)[C:25]([NH:27][CH3:28])=[O:26]>CS(C)=O>[CH3:28][NH:27][C:25](=[O:26])[C:24]1[CH:29]=[C:20]([NH:10][CH:4]2[CH:5]3[CH2:8][CH2:9][N:2]([CH2:7][CH2:6]3)[CH2:3]2)[CH:21]=[CH:22][C:23]=1[N+:30]([O-:32])=[O:31]

Participants

5

Reactant 3

HCID 184012826530-09-2HCID 442030775-Fluoro-N-methyl-2-nitrobenzamide2×HCID 68176228HCID 68176228, compound

Product 1

HCID 67115295HCID 67115295, compoundYield 26.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of quinuclidin-3-amine hydrochloride (1.06 g, 5.30 mmol) and polymer supported dimethylperhydro-1,3,2-diazaphosphorine (7.0 g, 15.4 mmol) in DMSO (50 mL) was added 5-fluoro-N-methyl-2-nitrobenzamide (Intermediate 3A) (1 g, 5.05 mmol) and reaction heated at 60° C. for 72 hours. The resin was removed by filtration and washed thoroughly with methanol and dichloromethane. The filtrate was purified using a 20 g SCX cartridge followed by trituration with dichloromethane/methanol/diethyl ether to afford N-methyl-2-nitro-5-(quinuclidin-3-ylamino)benzamide (0.41 g, 1.36 mmol).

Workup

  1. additionwas added
  2. customThe resin was removed by filtration
  3. washwashed thoroughly with methanol and dichloromethane
  4. customThe filtrate was purified

Sources & evidence

ORD record
ord-5c6af0e6651d4893922c2bc8eb4fb08b
Source dataset
uspto-grants-2014_09
Patent number
US08841289B2

Reaction notes

Loading…