2-Dimethylaminopyridine → HCID 21472729, compound

HRID 2260739Notes

Reaction equation

HRID 2260739 reaction equation
C1C=C(O[C:8](OC2N=CC=CC=2)=[S:9])N=CC=1.CN(C1C=CC=CN=1)C.[NH2:26][C:27]1[CH:42]=[C:41]([F:43])[C:30]2[N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH:32]=[N:33][C:29]=2[C:28]=1[CH3:44]>C(Cl)Cl>[C:37]([O:36][C:34]([N:31]1[C:30]2[C:41]([F:43])=[CH:42][C:27]([N:26]=[C:8]=[S:9])=[C:28]([CH3:44])[C:29]=2[N:33]=[CH:32]1)=[O:35])([CH3:39])([CH3:40])[CH3:38]

Participants

5

Reactant 3

HCID 218852-DimethylaminopyridineHCID 719784O,O-Dipyridin-2-yl carbonothioateHCID 18785142HCID 18785142, compound

Product 1

HCID 21472729HCID 21472729, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of di-2-pyridyl thionocarbonate (0.393 mg) and dimethylaminopyridine (0.01 g) in methylene chloride (100 mL) is added dropwise over 30 minutes a solution of 5-amino-1-tert-butoxycarbonyl-7-fluoro-4-methylbenzimidazole (0.409 g) in methylene chloride (70 mL). The mixture is stirred at room temperature for 3 hours then rotary evaporated. The residue is purified by flash chromatography on silica gel, eluting with 10% ethyl acetate/hexane to afford 1 -tert-butoxycarbonyl-7-fluoro-4-methyl-5-benzimidazolylisothiocyanate as a white solid.

Workup

  1. customThe residue is purified by flash chromatography on silica gel
  2. washeluting with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-b89d6e4933fa41f0bf5a43a9153b4dba
Source dataset
uspto-grants-1995_12
Patent number
US05478858

Reaction notes

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