O,O-Dipyridin-2-yl carbonothioate → HCID 21472729, compound

HRID 2295056Notes

Reaction equation

HRID 2295056 reaction equation
C1C=C(O[C:8](OC2N=CC=CC=2)=[S:9])N=CC=1.[NH2:17][C:18]1[CH:33]=[C:32]([F:34])[C:21]2[N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:23]=[N:24][C:20]=2[C:19]=1[CH3:35]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:28]([O:27][C:25]([N:22]1[C:21]2[C:32]([F:34])=[CH:33][C:18]([N:17]=[C:8]=[S:9])=[C:19]([CH3:35])[C:20]=2[N:24]=[CH:23]1)=[O:26])([CH3:30])([CH3:31])[CH3:29]

Participants

5

Reactant 2

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

Product 1

HCID 21472729HCID 21472729, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of di-2-pyridyl thionocarbonate (0.393 mg) and 4-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-89a0f6035bdd41988e5089f8136107c1
Source dataset
uspto-grants-1997_11
Patent number
US05691370

Reaction notes

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