Acetonitrile → HCID 86729758, compound

HRID 2272600Notes

Reaction equation

HRID 2272600 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:32])[CH2:11][S:12][CH2:13][C:14]([NH:16][C:17]2[CH:18]=[CH:19][C:20]3[N:21]([CH2:30][CH3:31])[C:22]4[C:27]([C:28]=3[CH:29]=2)=[CH:26][CH:25]=[CH:24][CH:23]=4)=[O:15])=[CH:5][CH:4]=1)#[N:2].C(#N)C.I([O-])(=O)(=O)=[O:37].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:32])[CH2:11][S:12]([CH2:13][C:14]([NH:16][C:17]2[CH:18]=[CH:19][C:20]3[N:21]([CH2:30][CH3:31])[C:22]4[C:27]([C:28]=3[CH:29]=2)=[CH:26][CH:25]=[CH:24][CH:23]=4)=[O:15])=[O:37])=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 24477Sodium ThiosulfateHCID 23667635Sodium periodateHCID 86729745HCID 86729745, compound

Product 1

HCID 86729758HCID 86729758, compoundYield 23.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-({2-[(4-cyanophenyl)amino]-2-oxoethyl}sulfanyl)-N-(9-ethyl-9H-carbazol-3-yl)acetamide (55 mg, 0.12 mmol) in a mixed solvent of acetonitrile (4 mL) and water (2 mL) was added sodium periodate (29.2 mg, 0.14 mmol), and the mixture was stirred at room temperature for 18 days. Aqueous sodium thiosulfate solution was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with aqueous sodium carbonate solution, and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by preparative HPLC to give the title compound (13 mg, 0.028 mmol, 23%) as a pale-yellow powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with aqueous sodium carbonate solution
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-bc9d279ca192459b952533ae1dfaa476
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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