Dimethyl Sulfoxide → HCID 118666045, compound

HRID 630498Notes

Reaction equation

HRID 630498 reaction equation
C(=O)([O-])[O-:2].[K+].[K+].OO.CSC1[C:19]2[C:14](=[CH:15][C:16]([C:20]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[O:21])=[CH:17][CH:18]=2)[N:13]([C:28]2[N:33]=[CH:32][C:31]([C:34]3[S:38][CH:37]=[C:36]([C:39]#[N:40])[CH:35]=3)=[CH:30][N:29]=2)[CH:12]=1.[CH3:41][S:42]([CH3:44])=[O:43]>O>[CH3:41][S:42]([C:44]1[C:19]2[C:14](=[CH:15][C:16]([C:20]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[O:21])=[CH:17][CH:18]=2)[N:13]([C:28]2[N:33]=[CH:32][C:31]([C:34]3[S:38][CH:37]=[C:36]([C:39]([NH2:40])=[O:2])[CH:35]=3)=[CH:30][N:29]=2)[CH:12]=1)=[O:43]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 118666272HCID 118666272, compound

Product 1

HCID 118666045HCID 118666045, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Potassium carbonate (90 mg, 0.650 mmol, 1.5 eq) and hydrogen peroxide (30%, 2.0 mL) were added at room temperature to a stirred solution of 5-(2-(3-(methylthio)-6-(morpholine-4-carbonyl)-1H-indol-1-yl)pyrimidin-5-yl)thiophene-3-carbonitrile (precursor of synthesis example 195, 200 mg, 0.433 mmol, 1.0 eq) in DMSO (2 mL). The reaction mixture was stirred at this temperature for 48 h and then diluted with water (10 mL). The precipitating solid was filtered off, washed with water, and dried under vacuum. The remnant was purified by column chromatography [silica gel 100-200 mesh, dichloromethane with 2% methanol].

Workup

  1. filtrationThe precipitating solid was filtered off
  2. washwashed with water
  3. customdried under vacuum
  4. customThe remnant was purified by column chromatography [silica gel 100-200 mesh, dichloromethane with 2% methanol]

Sources & evidence

ORD record
ord-8b5e7b5b76f14b5b91c2cf6c538da586
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

Loading…