O-Phenylenediamine → HCID 178431476, compound

HRID 658119Notes

Reaction equation

HRID 658119 reaction equation
CS[C:3](SC)=[C:4]([C:21]([C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1)=[O:22])[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C@@H:13]2[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14]2)[C:8]=1[F:20])=[O:6].[C:31]1([NH2:38])[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[NH2:37]>C(O)C>[NH:37]1[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[NH:38][C:3]1=[C:4]([C:21]([C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1)=[O:22])[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C@@H:13]2[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14]2)[C:8]=1[F:20])=[O:6]

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 86643280HCID 86643280, compound

Product 1

HCID 178431476HCID 178431476, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 0.12 g portion of 2-[bis(methylsulfanyl)methylene]-1-[3-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-fluorophenyl]-3-pyridin-3-yl-propan-1,3-dione and 36 mg of 1,2-phenylenediamine were dissolved in 8 ml of ethanol and heated under reflux for 3 hours. After concentration of the reaction liquid, the thus formed residue was purified by a silica gel column chromatography to obtain 0.12 g (97%) of 2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-1-{3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-fluorophenyl}-3-pyridin-3-yl-propane-1,3-dione as a yellow solid from an ethyl acetate-hexane (3:1) eluate. FA: 460

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hours
  3. customAfter concentration of the reaction liquid
  4. customthe thus formed residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-0b98a4b92a1e4f5bb1a1c6cdaeaaee72
Source dataset
uspto-grants-2011_12
Patent number
US08076367B2

Reaction notes

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