Methanesulfonamide → HCID 72613070, compound

HRID 2181132Notes

Reaction equation

HRID 2181132 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[N:9]([O:21][CH3:22])[C:10](=[O:20])[CH:11]=[C:12]2[C:16](=O)[O:15]C(C)(C)[O:13]2)=[CH:4][CH:3]=1.[CH3:30][S:31]([NH2:34])(=[O:33])=[O:32].N12CCCN=C1CCCCC2>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:9]([O:21][CH3:22])[C:10](=[O:20])[CH:11]=[C:12]([OH:13])[C:16]([NH:34][S:31]([CH3:30])(=[O:33])=[O:32])=[O:15])[C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 72879MethanesulfonamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 73855572HCID 73855572, compound

Product 1

HCID 72613070HCID 72613070, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-[bis-(4-fluoro-phenyl)-methyl]-2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-methoxy-acetamide (0.175 g, 0.43 mmol) and methanesulfonamide (0.062 g, 0.52 mmol) in anhydrous N,N-dimethylformamide (3 ml) was treated at 25° C. with 1,8-diazabicyclo[5.4.0]undec-7-ene (0.1 ml). After 1 h, the reaction mixture was then quenched by the addition of ethyl acetate and 1 N hydrochloric acid. The organic phase was washed successively with water and brine and dried over anhydrous magnesium sulfate. Evaporation of the solvent and chromatography of the residue on silica gel (elution ethyl acetate-methanol 0-20%) gave 0.129 g (67% yield) of the title amide as a white solid. 1H NMR (400 MHz, DMSO) δ: mixture of rotamers: 2.78, 2.81,2.87 and 2.88 (3H, 4 s, SO2CH3), 3.15, 3.16, 3.18 and 3.20 (3H, 4 s, OCH3), 6.22, 6.25 and 6.27 (1H, 3 s, CH), 6.75-6.89 (1H, m, CH), 7.17-7.54 (8H, m, aromatics). HRMS (ESI/neg) calculated for C19H17F2N2O6S, [M−H]−: 439.077540; found: 439.077728.

Workup

  1. customthe reaction mixture was then quenched by the addition of ethyl acetate and 1 N hydrochloric acid
  2. washThe organic phase was washed successively with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customEvaporation of the solvent and chromatography of the residue on silica gel (elution ethyl acetate-methanol 0-20%)

Sources & evidence

ORD record
ord-c1adae0e590a4542988e161dbbd30a8d
Source dataset
uspto-grants-2005_05
Patent number
US06890942B2

Reaction notes

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