Pyridine → HCID 22010636, compound

HRID 323161Notes

Reaction equation

HRID 323161 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:37]=[CH:36][C:20]([C:21]([N:23]([CH3:35])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30][CH2:31][CH2:32][CH2:33][OH:34])=[O:22])=[CH:19][CH:18]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[N:38]1[CH:43]=[CH:42]C=[CH:40][CH:39]=1.Cl[C:45](OC1C=CC([N+]([O-])=O)=CC=1)=[O:46].[CH3:57][N:58]1CCNCC1>ClCCl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([C:21]([N:23]([CH3:35])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30][CH2:31][CH2:32][CH2:33][O:34][C:45]([N:38]4[CH2:39][CH2:40][N:58]([CH3:57])[CH2:42][CH2:43]4)=[O:46])=[O:22])=[CH:36][CH:37]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 531671-MethylpiperazineHCID 821294-Nitrophenyl chloroformateHCID 22010692HCID 22010692, compound

Product 1

HCID 22010636HCID 22010636, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(3-hydroxypropoxy)phenyl]benzamide (300 mg) in dichloromethane (15 ml) was treated with pyridine (95.8 mg) and p-nitrophenyl chloroformate (183 mg). After 4.5 hours, 1-methylpiperazine (303 mg) was added to the reaction mixture and stirred for a further 1 hour at ambient temperature. After concentration, the residue was dissolved in ethyl acetate and washed with saturated sodium hydrogen carbonate solution and brine, dried over sodium sulfate, concentrated, and purified by silica gel column chromatography (SiO2; 30 g, 3% methanol in dichloromethane) to give 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-[3-(4-methylpiperazin-1-carbonyloxy)propoxy]phenyl]benzamide (200 mg) as white amorphous.

Workup

  1. concentrationAfter concentration
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with saturated sodium hydrogen carbonate solution and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography (SiO2; 30 g, 3% methanol in dichloromethane)

Sources & evidence

ORD record
ord-0cb9e8ba924b448686f85f3acd3001bf
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Reaction notes

Loading…