Sodium Thiosulfate → HCID 15949406, compound

HRID 548688Notes

Reaction equation

HRID 548688 reaction equation
[Cl:1][C:2]1[C:12]2[O:11][CH2:10][CH2:9][N:8]([CH3:13])[C:7](=[O:14])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:15][C:16]1[CH:17]=[C:18]([CH:29]=[C:30]([O:32][C@@H:33]([CH3:37])[CH2:34][O:35]C)[CH:31]=1)[C:19]([NH:21][C:22]1[CH:26]=[CH:25][N:24]([CH2:27][CH3:28])[N:23]=1)=[O:20].C[Si](I)(C)C.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C>[Cl:1][C:2]1[C:12]2[O:11][CH2:10][CH2:9][N:8]([CH3:13])[C:7](=[O:14])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:15][C:16]1[CH:17]=[C:18]([CH:29]=[C:30]([O:32][C@@H:33]([CH3:37])[CH2:34][OH:35])[CH:31]=1)[C:19]([NH:21][C:22]1[CH:26]=[CH:25][N:24]([CH2:27][CH3:28])[N:23]=1)=[O:20]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 85247Trimethylsilyl iodideHCID 15949401HCID 15949401, compound

Product 1

HCID 15949406HCID 15949406, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3-[(9-chloro-4-methyl-5-oxo-2,3,4,5-tetrahydro-1,4-benzoxazepin-8-yl)oxy]-N-(1-ethyl-1H-pyrazol-3-yl)-5-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}benzamide (300 mg, 0.57 mmol) in acetonitrile (10 mL) was treated with trimethylsilyl iodide (0.404 mL) and stirred at RT under argon for 3 hours. Sodium thiosulphate solution (30 mL) was added to quench the reaction and 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 by column chromatography on silica, eluting with 50-100% ethyl acetate in hexanes, gave the desired compound as a pale yellow solid (230 mg).

Workup

  1. customto quench
  2. customthe reaction and mixture
  3. extractionwas 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 by column chromatography on silica
  9. washeluting with 50-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-d5d012069b6141498258c260652ed24c
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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