Sulfuric Acid → HCID 87054984, compound

HRID 2201584Notes

Reaction equation

HRID 2201584 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:20]=[C:19]([N:21]([CH3:26])[S:22]([CH3:25])(=[O:24])=[O:23])[C:18]([C:27]4[N:32]=[C:31]([C:33]([NH:35][C@@H:36]([C:38]5[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=5)[CH3:37])=[O:34])[C:30]([OH:45])=[CH:29][CH:28]=4)=[CH:17][C:11]=3[C:12]=2[C:13](=[O:16])[NH:14][CH3:15])=[CH:4][CH:3]=1.O1COCO[CH2:47]1.OS(O)(=O)=O.S([O-])([O-])(=O)=O.[Na+].[Na+].[OH-].[Na+]>ClCCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:20]=[C:19]([N:21]([CH3:26])[S:22]([CH3:25])(=[O:24])=[O:23])[C:18]([C:27]4[CH:28]=[CH:29][C:30]5[O:45][CH2:47][N:35]([C@@H:36]([C:38]6[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=6)[CH3:37])[C:33](=[O:34])[C:31]=5[N:32]=4)=[CH:17][C:11]=3[C:12]=2[C:13]([NH:14][CH3:15])=[O:16])=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 80811,3,5-TrioxaneHCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 117771077HCID 117771077, compound

Product 1

HCID 87054984HCID 87054984, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

(R)-6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)-N-(1-(4-fluorophenyl)ethyl)-3-hydroxypicolinamide (80 mg, 0.13 mmol), 1,3,5-trioxane (114 mg, 1.26 mmol), H2SO4 (20 μl, 0.38 mmol) and sodium sulfate (159 mg, 1.26 mmol) in 1,2-dichloroethane (5 ml) were sealed in a tube. The mixture was microwaved at 80° C. for 1 h. 1N NaOH (10 ml) was added and the mixture extracted with ethyl acetate, dried over Na2SO4, filtered and concentrated in vacuo. Preparative TLC gave (R)-2-(4-fluorophenyl)-5-(3-(1-(4-fluorophenyl)ethyl)-4-oxo-3,4-dihydro-2H-pyrido[2,3-e][1,3]oxazin-6-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (17 mg, yield: 21%). MS (M+H)+: 647.

Workup

  1. customThe mixture was microwaved at 80° C. for 1 h
  2. extractionthe mixture extracted with ethyl acetate
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7dd0909ddde94f7ea3dc3db943985ef9
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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