HCID 10679101, compound → HCID 15463736, compound

HRID 1597313Notes

Reaction equation

HRID 1597313 reaction equation
[C:1]1([NH:7][C:8](=[O:12])OCCl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:13][C:14]1[C:35]([Cl:36])=[CH:34][C:17]([C:18]([NH:20][CH:21]2[CH2:26][CH2:25][N:24]([CH2:27][CH:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[CH2:23][CH2:22]2)=[O:19])=[C:16]([O:37][CH3:38])[CH:15]=1>C(O)C>[NH2:13][C:14]1[C:35]([Cl:36])=[CH:34][C:17]([C:18]([NH:20][CH:21]2[CH2:26][CH2:25][N:24]([CH2:27][CH:28]3[CH2:29][CH2:30][N:31]([C:8](=[O:12])[NH:7][C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH2:32][CH2:33]3)[CH2:23][CH2:22]2)=[O:19])=[C:16]([O:37][CH3:38])[CH:15]=1

Participants

4

Reactant 2

HCID 10679101HCID 10679101, compoundHCID 10937790HCID 10937790, compound

Product 1

HCID 15463736HCID 15463736, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of chloromethyl N-phenylcarbamate (220 mg), which is prepared by the method disclosed in Synth. Commun., 1996, 26, 4253, in ethanol (20 ml) is added dropwise a solution of 4-amino-5-chloro-2-methoxy-N-[1-(4-piperidinylmethyl)-4-piperidinyl]benzamide (910 mg) in ethanol (10 ml) at room temperature, and the mixture is stirred at room temperature for 7 hours. The mixture is concentrated to dryness under reduced pressure, and the residue is dissolved in chloroform, washed with water and a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent is evaporated under reduced pressure. The residue is purified by silica gel column chromatography (eluent; chloroform:methanol=30:1) to give the desired compound (480 mg) as white amorphous.

Workup

  1. concentrationThe mixture is concentrated to dryness under reduced pressure
  2. dissolutionthe residue is dissolved in chloroform
  3. washwashed with water
  4. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  5. customthe solvent is evaporated under reduced pressure
  6. customThe residue is purified by silica gel column chromatography (eluent; chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-a11a04276dde4e81b34d5cc7ee7a253b
Source dataset
uspto-grants-2001_09
Patent number
US06294555B1

Reaction notes

Loading…