Pyridine → HCID 22010872, compound

HRID 323159Notes

Reaction equation

HRID 323159 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:39]=[CH:38][C:20]([C:21]([N:23]([CH3:37])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][NH2:36])=[O:22])=[CH:19][CH:18]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:47]([O:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:48]>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]([CH3:37])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][NH:36][C:47]([O:49][C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)=[O:48])=[O:22])=[CH:38][CH:39]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 22011014HCID 22011014, compound

Product 1

HCID 22010872HCID 22010872, compoundYield 63.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(5-aminopentyloxy)phenyl]benzamide (750 mg) in dichloromethane (30 ml) was treated with pyridine (681 mg) and phenyl chloroformate (675 mg). After 18 hours, the solvent was removed and the residue was dissolved in ethyl acetate, washed with 1N hydrochloric acid, water, saturated sodium hydrogen carbonate solution and brine, dried over sodium sulfate, concentrated, and purified by silica gel column chromatography (SiO2; 50 g, 1% methanol in dichloromethane) to give 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(5-phenoxycarbonylaminopentyloxy)phenyl]benzamide (590 mg).

Workup

  1. customthe solvent was removed
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with 1N hydrochloric acid, water, saturated sodium hydrogen carbonate solution and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography (SiO2; 50 g, 1% methanol in dichloromethane)

Sources & evidence

ORD record
ord-d27eb74558dc4befbb3fe684d1d6c392
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Reaction notes

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