Pyridine → HCID 70571510, compound

HRID 2403580Notes

Reaction equation

HRID 2403580 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][N:15]([CH3:27])[C:16](=[O:26])[CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:9]=2)=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:34][N:35]([CH3:39])[C:36](Cl)=[O:37]>C(Cl)Cl>[CH3:34][N:35]([CH3:39])[C:36]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][N:15]([CH3:27])[C:16](=[O:26])[CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:24])[CH3:22])[CH:9]=2)=[CH:4][CH:3]=1)=[O:37]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6598Dimethylcarbamoyl ChlorideHCID 70570127HCID 70570127, compound

Product 1

HCID 70571510HCID 70571510, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (2-{[(4′-aminobiphenyl-3-yl)methyl](methyl)amino}-2-oxoethyl)carbamate (200 mg) and pyridine (64 mg) were dissolved in methylene chloride (6 ml), followed by ice-cooling. Dimethylcarbamoylchloride (64 mg) was added thereto, followed by warming to room temperature and stirring for 1 hour. The reaction mixture was subjected to liquid separation with CHCl3 and water. The organic layer was separated, and then the aqueous layer was extracted with CHCl3 again. These organic layers were combined and dried over sodium sulfate, and the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (2% MeOH/CHCl3) to obtain tert-butyl {2-[({4′-[(dimethylcarbamoyl)amino]biphenyl-3-yl}methyl)(methyl)amino]-2-oxoethyl}carbamate (220 mg) as a colorless oil.

Workup

  1. temperaturecooling
  2. customThe reaction mixture was subjected to liquid separation with CHCl3 and water
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with CHCl3 again
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was evaporated
  7. customThe obtained residue was purified by silica gel column chromatography (2% MeOH/CHCl3)

Sources & evidence

ORD record
ord-b3a9c3c952a446aba643e46d54d7a095
Source dataset
uspto-grants-2014_08
Patent number
US08802679B2

Reaction notes

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