Sodium Thiosulfate → HCID 69794758, compound

HRID 658506Notes

Reaction equation

HRID 658506 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19]([NH:21][C:22]3[CH:35]=[CH:34][C:25]4[O:26][C:27]([F:33])([F:32])[O:28][C:29]([F:31])([F:30])[C:24]=4[CH:23]=3)=[O:20])=[C:14](SC)[CH:13]=2)[CH:8]=[CH:7][N:6]=1)=[O:4].[CH:38]1C=C(Cl)C=C(C(OO)=O)C=1.[S:49]([O-:53])([O-])(=[O:51])=S.[Na+].[Na+]>C(Cl)Cl.C1COCC1>[CH3:1][NH:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:13]=[CH:14][C:15]([NH:18][C:19]([NH:21][C:22]3[CH:35]=[CH:34][C:25]4[O:26][C:27]([F:32])([F:33])[O:28][C:29]([F:30])([F:31])[C:24]=4[CH:23]=3)=[O:20])=[C:16]([S:49]([CH3:38])(=[O:53])=[O:51])[CH:17]=2)[CH:8]=[CH:7][N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 59987500HCID 59987500, compound

Product 1

HCID 69794758HCID 69794758, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

To N-methyl-4-[3-(methylthio)-4-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)-amino]carbonyl}amino)phenoxy]pyridine-2-carboxamide (150 mg, 0.28 mmol) in anhydrous 1:1 v/v DCM/THF (3.0 mL) at 0° C. was added mCPBA (162.7 mg, 0.61 mmol, 2.2 eq, and the reaction mixture was stirred at RT for 17 h. The reaction mixture was poured into aqueous saturated sodium thiosulfate solution and extracted with EtOAc (3×100 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and evaporated under reduced pressure to give 73.3 mg (46.1%) of the title compound as a white solid. 1H-NMR (DMSO-d6) δ 10.31 (s, 1H), 8.81 (q, J=5.4 Hz, 1H), 8.71 (s, 1H), 8.55 (d, J=5.7 Hz, 1H), 8.23 (d, J=9.0 Hz, 1H), 8.15 (d, J=2.4 Hz, 1H), 7.70 to 7.59 (m, 3H), 7.47 (s, 1H), 7.45 (d, J=6.9 Hz, 1H), 7.21 (dd, J=5.4, 2.4 Hz, 1H), 3.37 (s, 3H), 2.79 (d, J=5.1 Hz, 3H); MS LC-MS (M+H)+=571.1, RT=3.81 min; m.p. 222-223.5° C.

Workup

  1. extractionextracted with EtOAc (3×100 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f6280109a61e4f9cabfce6793e6ecebc
Source dataset
uspto-grants-2011_12
Patent number
US08076488B2

Reaction notes

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