Sodium Thiosulfate → HCID 86721366, compound

HRID 869536Notes

Reaction equation

HRID 869536 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2=[C:6]([CH:35]=1)[O:7][CH2:8][C:9]1[CH:19]=[C:18]([CH2:20][N:21]3[C:25]4[CH:26]=[CH:27][CH:28]=[C:29](SC)[C:24]=4[N:23]=[C:22]3[CH2:32][O:33][CH3:34])[CH:17]=[CH:16][C:10]=1/[C:11]/2=[C:12](/[CH3:15])\[C:13]#[N:14].Cl[C:37]1C=CC=C(C(OO)=O)C=1.[S:47]([O-:51])([O-])(=[O:49])=S.[Na+].[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]2=[C:6]([CH:35]=1)[O:7][CH2:8][C:9]1[CH:19]=[C:18]([CH2:20][N:21]3[C:25]4[CH:26]=[CH:27][CH:28]=[C:29]([S:47]([CH3:37])(=[O:51])=[O:49])[C:24]=4[N:23]=[C:22]3[CH2:32][O:33][CH3:34])[CH:17]=[CH:16][C:10]=1/[C:11]/2=[C:12](/[CH3:15])\[C:13]#[N:14]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 86721367HCID 86721367, compound

Product 1

HCID 86721366HCID 86721366, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(E)-2-(3-fluoro-8-{[2-(methoxymethyl)-4-(methylthio)-1H-benzo[d]imidazol-1-yl]methyl}dibenzo[b,e]oxepin-11(6H)-ylidene)propionitrile (120 mg, 0.25 mmol) obtained in Reference Example 2M was dissolved in methylene chloride (1.2 mL), m-chloroperbenzoic acid (227 mg, 0.989 mmol) was added at 0° C., and the mixture was stirred at room temperature for 4 hr. The reaction was discontinued with aqueous sodium thiosulfate solution, the mixture was extracted with chloroform, and the extract was dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform/methanol=10/1 v/v) to give (E)-2-(3-fluoro-8-{[2-(methoxymethyl)-4-(methylsulfonyl)-1H-benzo[d]imidazol-1-yl]methyl}dibenzo[b,e]oxepin-11(6H)-ylidene)propionitrile (79 mg, 62%).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialthe extract was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol=10/1 v/v)

Sources & evidence

ORD record
ord-8738b99b11e1491eb320a4f7fce06be0
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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