Dimethylformamide → HCID 86760399, compound

HRID 348486Notes

Reaction equation

HRID 348486 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:12]([CH3:23])=[N:13][C:14]([S:17]([CH2:19][C:20](=[O:22])[NH2:21])=[O:18])=[N:15][CH:16]=2)=[O:10])=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:32])C=1.CN(C=O)C>ClCCl.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:12]([CH3:23])=[N:13][C:14]([S:17]([CH2:19][C:20](=[O:22])[NH2:21])(=[O:32])=[O:18])=[N:15][CH:16]=2)=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 70297m-Chloroperbenzoic acidHCID 86760398HCID 86760398, compound

Product 1

HCID 86760399HCID 86760399, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-carbamoylmethylsulfinyl-4-methylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide (as prepared above, 42 mg, 0.12 mmol) and m-CPBA (47 mg, 0.27 mmol) in 2 mL of 1:1 dichloromethane:DMF was stirred at ambient temperature for 3 days. The solution was diluted with 40 mL of 1:1 ethyl acetate:hexane and sequentially washed with 2×10 mL 5% NaHCO3(aq), 10 mL 0.1 M HCl(aq) and 10 mL brine. The organic layer was dried using Na2SO4 and concentrated to a white solid which was triturated with 10 mL of 1:1 dichloromethane:hexane, yielding 8 mg (19%) of the titled compound as a white solid.

Workup

  1. washhexane and sequentially washed with 2×10 mL 5% NaHCO3(aq), 10 mL 0.1 M HCl(aq) and 10 mL brine
  2. customThe organic layer was dried
  3. concentrationconcentrated to a white solid which
  4. customwas triturated with 10 mL of 1:1 dichloromethane

Sources & evidence

ORD record
ord-3a4189f4b6e644ffa80870d06510c911
Source dataset
uspto-grants-2007_02
Patent number
US07176310B1

Reaction notes

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