Sodium Thiosulfate → HCID 15949498, compound

HRID 548703Notes

Reaction equation

HRID 548703 reaction equation
[CH2:1]([N:3]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:36])[C:10]2[CH:15]=[C:14]([O:16][C:17]3[CH:29]=[CH:28][C:20]4[C:21](=[O:27])[N:22]([CH3:26])[CH2:23][CH2:24][O:25][C:19]=4[CH:18]=3)[CH:13]=[C:12]([O:30][C@@H:31]([CH3:35])[CH2:32][O:33]C)[CH:11]=2)=[N:4]1)[CH3:2].C[Si](I)(C)C.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C>[CH2:1]([N:3]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:36])[C:10]2[CH:15]=[C:14]([O:16][C:17]3[CH:29]=[CH:28][C:20]4[C:21](=[O:27])[N:22]([CH3:26])[CH2:23][CH2:24][O:25][C:19]=4[CH:18]=3)[CH:13]=[C:12]([O:30][C@@H:31]([CH3:35])[CH2:32][OH:33])[CH:11]=2)=[N:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 85247Trimethylsilyl iodideHCID 15949403HCID 15949403, compound

Product 1

HCID 15949498HCID 15949498, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of N-(1-ethyl-1H-pyrazol-3-yl)-3-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-5-[(4-methyl-5-oxo-2,3,4,5-tetrahydro-1,4-benzoxazepin-8-yl)oxy]benzamide (125 mg, 0.25 mmol) in acetonitrile (5 mL) was treated with trimethylsilyl iodide (0.178 mL) drop wise and stirred at RT under argon for 2.5 hours. Aqueous sodium thiosulphate solution (30 mL) was added to quench the reaction and the mixture was extracted with ethyl acetate (3×30 mL). The combined organic extracts were dried (MgSO4), filtered and evaporated to give a yellow oil. Purification was carried out by column chromatography on silica, eluting with 50-100% ethyl acetate in isohexane, to give the desired compound as a pale yellow foam (50 mg).

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe mixture was extracted with ethyl acetate (3×30 mL)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give a yellow oil
  8. customPurification
  9. washeluting with 50-100% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-c8c4d1e9fa0147fb80fe99e0b363766b
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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