HCID 66965669, compound → HCID 66965546, compound

HRID 1514872Notes

Reaction equation

HRID 1514872 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[NH2:18])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=1)=[O:6].[CH2:19]([O:21][C:22](=[O:33])[NH:23][C:24]1[CH:29]=[CH:28][C:27]([CH:30]=O)=[C:26]([CH3:32])[CH:25]=1)[CH3:20]>CO>[CH2:19]([O:21][C:22](=[O:33])[NH:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[NH:1][C:2]3[CH:3]=[C:4]([C:5](=[O:6])[NH:7][C:8]4[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=4)[CH:15]=[CH:16][C:17]=3[N:18]=2)=[C:26]([CH3:32])[CH:25]=1)[CH3:20]

Participants

4

Reactant 2

HCID 66965669HCID 66965669, compoundHCID 86651255HCID 86651255, compound

Product 1

HCID 66965546HCID 66965546, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3,4-diamino-N-(3-chloro-phenyl)-benzamide (0.4 mL in 0.2 M DMSO solution), (4-formyl-3-methyl-phenyl)-carbamic acid ethyl ester (0.4 mL in 0.2 M toluene solution) and FeCl3 (0.2 mL in 0.02M THF solution) was stirred in open air at ambient temperature overnight. The mixture was then diluted by MeOH and the whole was loaded onto a solid phase extraction (SPE) cartridge that contained strong cation exchange (SCX) (1 g media in 6 mL cartridge, United Chemical Technology). Wash-to-waste (5 mL MeOH) was followed by elute-to-collect (5 mL 20:2:1 ethyl acetate-MeOH-Et3N) and, after evaporation of volatiles, the crude was further purified by silica gel column chromatography to give {4-[6-(3-Chloro-phenylcarbamoyl)-1H-benzoimidazol-2-yl]-3-methyl-phenyl}-carbamic acid ethyl ester: MS (m/z) 449 (M+1).

Workup

  1. extractionthe whole was loaded onto a solid phase extraction (SPE) cartridge that
  2. washWash-to-waste (5 mL MeOH)
  3. customby elute-to-collect (5 mL 20:2:1 ethyl acetate-MeOH-Et3N)
  4. customafter evaporation of volatiles
  5. customthe crude was further purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2642e3b931e84487835f9a2fffbc507e
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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