Dimethyldioxirane → HCID 54575146, compound

HRID 2190159Notes

Reaction equation

HRID 2190159 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]2[C:18]([C:19]([NH:21][CH3:22])=[O:20])=[C:17]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[O:16][C:7]2=[N:8][C:9]=1[N:10]([CH3:15])[S:11]([CH3:14])(=[O:13])=[O:12])[CH:2]=[CH2:3].CC1(C)O[O:32]1>CC(C)=O>[F:29][C:26]1[CH:27]=[CH:28][C:23]([C:17]2[O:16][C:7]3=[N:8][C:9]([N:10]([CH3:15])[S:11]([CH3:14])(=[O:13])=[O:12])=[C:4]([CH2:1][CH:2]4[CH2:3][O:32]4)[CH:5]=[C:6]3[C:18]=2[C:19]([NH:21][CH3:22])=[O:20])=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 115197DimethyldioxiraneHCID 54576012HCID 54576012, compound

Product 1

HCID 54575146HCID 54575146, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5-allyl-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)furo[2,3-b]pyridine-3-carboxamide was stirred with a solution of dimethyldioxirane in acetone until LCMS indicated complete conversion to product. The solution was evaporated to dryness to afford the title compound. MS (ESI) m/z 434.1 (M+1). NMR (400 MHz, CD3CN) δ 8.23 (s, 1H), 8.04-8.00 (m, 2H), 7.33-7.29 (m, 2H), 6.83 (br s, 1H), 3.28 (s, 3H), 3.26-3.24 (m, 2H), 3.16 (s, 3H), 3.05-2.99 (m, 1H), 2.92-2.90 (d, 3H), 2.82-2.79 (m, 1H), 2.63-2.61 (m, 1H)

Workup

  1. customThe solution was evaporated to dryness

Sources & evidence

ORD record
ord-6698c2ba5bfc4244a97892761280f06f
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

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