Dimethyl Sulfoxide → HCID 57900435, compound

HRID 628093Notes

Reaction equation

HRID 628093 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:7][CH2:8][CH2:9][C:10]3[CH:16]=[C:15]([C:17]4[C:21]([C:22]5[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=5[F:29])=[N:20][NH:19][N:18]=4)[S:14][C:11]=3[C:12]=2[N:13]=1)#[N:2].CS(C)=[O:32].C(=O)([O-])[O-].[K+].[K+].O.OO.S(=O)(O)[O-].[Na+]>>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:7][CH2:8][CH2:9][C:10]3[CH:16]=[C:15]([C:17]4[C:21]([C:22]5[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=5[F:29])=[N:20][NH:19][N:18]=4)[S:14][C:11]=3[C:12]=2[N:13]=1)(=[O:32])[NH2:2]

Participants

7

Reactant 6

HCID 679Dimethyl SulfoxideHCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 23665763Sodium BisulfiteHCID 579001874-(2-cyano-6,7-dihydropyrido[3,2-b]thieno[2,3-d]oxepin-9-yl)-5-(2,4-difluorophenyl)-2H-1,2,3-triazole

Product 1

HCID 57900435HCID 57900435, compoundYield 27%

Conditions

Temperature
0 °C

Procedure

To a solution of 367 (70.0 mg, 0.172 mmol) in dimethyl sulfoxide (0.439 mL, 6.18 mmol) and treated with a solution of potassium carbonate (65.5 mg, 0.474 mmol;) in water (0.433 mL, 24.0 mmol;). After cooling at 0° C., hydrogen peroxide (0.540 mL, 7.04 mmol) was added slowly. The reaction was complete by LCMS at 15 min. Saturated sodium bisulfite (0.894 g, 8.59 mmol) was added and the reaction mixture extracted into ethyl acetate. The organics were washed with brine, dried over sodium sulfate and concentrated to give crude C which was submitted to reverse-phase HPLC to give 379 (27% yield). MS: (ESI+)=426.1

Workup

  1. extractionthe reaction mixture extracted into ethyl acetate
  2. washThe organics were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customto give crude C which

Sources & evidence

ORD record
ord-7ca2c870c04f41b3b40a278dcb44bbdc
Source dataset
uspto-grants-2016_04
Patent number
US09309265B2

Reaction notes

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