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Potassium Carbonate → HCID 86705063, compound

HRID 1427308
Notes
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Reaction equation

HRID 1427308 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:14]2[C:22]3[C:17](=[C:18]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15]2)([CH2:12][CH3:13])[C:9](=O)[CH3:10])=[CH:4][CH:3]=1.Cl.[NH2:29][OH:30].C([O-])([O-])=O.[K+].[K+]>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:14]2[C:22]3[C:17](=[C:18]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15]2)([CH2:12][CH3:13])[C:9](=[N:29][OH:30])[CH3:10])=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 70560671HCID 70560671, compound

Product 1

HCID 86705063HCID 86705063, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of N-(1-(3-(4-chlorophenyl)-2-oxopentan-3-yl)-1H-indol-4-yl)methanesulfonamide (200 mg, 0.49 mmol), as described in Example 23 Step A, in EtOH (5 mL) was added hydroxylamine hydrochloride (68 mg, 0.99 mmol) and K2CO3 (137 mg, 0.99 mmol). The mixture was stirred at 130° C. under microwave for 2 h. After removing the solvent, the residue was dissolved in ethyl acetate (30 mL). The organic layer was washed with saturated sodium bicarbonate solution (10 mL) and brine (10 mL), dried over sodium sulfate, and then filtered. After removing the organic solvent, the residue was purified by silica gel chromatography eluting with PE/EA (10/1 to 5/1, v/v) to afford the title compound as a white solid. LC/MS m/z=441.9 [M+Na]+.

Workup

  1. customAfter removing the solvent
  2. dissolutionthe residue was dissolved in ethyl acetate (30 mL)
  3. washThe organic layer was washed with saturated sodium bicarbonate solution (10 mL) and brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customAfter removing the organic solvent
  7. customthe residue was purified by silica gel chromatography
  8. washeluting with PE/EA (10/1 to 5/1

Sources & evidence

ORD record
ord-b4a1497a37cd4ff0b0daebe2d5d53d14
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08933113B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes